H-GLU(OBZL)-NCA CAS#: 3190-71-4; 凯望编码 (ChemWhat Code): 85923
Identification
| 英文名 | H-GLU(OBZL)-NCA |
| IUPAC Name | benzyl 3-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]propanoate |
| 分子结构 |  |
| CAS编号 | 3190-71-4 |
| MDL Number | MFCD11046651 |
| 别名 | 5-benzyl L-glutamate N-carboxyanhydride, γ-benzyl ester L-glutamic acid-N-carboxylic acid anhydride, N-Carboxy-Oγ-benzyl-L-glutamic Acid Anhydride, (S)-4-(2-benzyloxycarbonylethyl)-1,3-oxazolidine-2,5-dione, L-glutamic acid benzyl ester five membered ring anhydride, γ-O-benzyl-L-glutamic acid N-carboxyanhydride, γ-benzyl-L-glutamic acid N-carboxylanhydride |
| 分子式 | C13H13NO5 |
| 分子量 | 263.25 |
| InChI | InChI=1S/C13H13NO5/c15-11(18-8-9-4-2-1-3-5-9)7-6-10-12(16)19-13(17)14-10/h1-5,10H,6-8H2,(H,14,17)/t10-/m0/s1 |
| InChI Key | UGCBVSDSTGUPBC-JTQLQIEISA-N |
| Canonical SMILES | C1=CC=C(C=C1)COC(=O)CCC2C(=O)OC(=O)N2 |
| Isomeric SMILES | C1=CC=C(C=C1)COC(=O)CC[C@H]2C(=O)OC(=O)N2 |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2013/280306 | BLOCK COPOLYMERS FOR STABLE MICELLES | 2013 |
| US2014/271885 | COPOLYMERS FOR STABLE MICELLE FORMULATIONS | 2014 |
Physical Data
| Appearance | White powder |
| Melting Point, °C | Solvent (Melting Point) |
| 92-93 | tetrahydrofuran, hexane |
| 94 | |
| 93-94 | tetrahydrofuran, hexane |
| 93-94 | ethyl acetate, n-heptane |
| Type (Optical Rotatory Power) | Concentration (Optical Rotatory Power) | Length of Path, cm | Solvent (Optical Rotatory Power) | Optical Rotatory Power, deg | Wavelength (Optical Rotatory Power), nm | Temperature (Optical Rotatory Power), °C |
| [alpha] | 1 g/100ml | 10 | tetrahydrofuran | -14.5 | 589 | 25 |
| [alpha] | 3.15 g/100ml | ethyl acetate | -16.8 | 589 | 23 | |
| [alpha] | -8.6 | 589 | 25 | |||
| [alpha] | c=3.78 | ethyl acetate | -18.2 | 589 | 25 | |
| [alpha] | c=3.65 | ethyl acetate | -17 | 589 | 29 | |
| [alpha] | c=3.78 | ethyl acetate | -11.2 | 589 | 23 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 400 | 1H NMR (400 MHz, CDCI3, 5, ppm): 7.40-7.31 (m, 5H, CHaromatic), 6.59 (s, 1H, NH), 5.13 (s, 2H, CH2O), 4.38 (ddd, J = 6.5, 5.4, 0.8 Hz, 1H, OCCHNH), 2.59 (t, J = 6.9 Hz, 2H, O(O)CCH2), 2.31-2.06 (m, 2H, CH2). |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 101 | 13C NMR (101 MHz,CDCI3, 5, ppm): 172.5, 169.5, 151.9, 135.3, 128.8, 128.7, 128.5, 67.2, 57.0, 30.0, 27.0. |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Original Text (IR Spectroscopy) |
| Bands | potassium bromide | in curve (B), new absorptions occurs at 1785 cm-1 and 1753 cm-1 |
| Bands | FT-IR: 1651,1737, 1790, 1856 and 1965 cm. |
Route of Synthesis (ROS)
| Conditions | Yield |
| With phosgene In tetrahydrofuran at 45 – 65℃; for 1.08333h; Experimental Procedure 2 EXAMPLE 2: PREPARATION OF L-GLUTAMIC ACID N-CARBOXYANHYDRIDE, y-BENZYL ESTER.; [0031] In this Example, a stirred mixture of 3.3 liters anhydrous tetrahydrofuran and 466 g (1.96 moles) L-glutamic acid, γ-benzyl ester, was purged with nitrogen below liquid surface at 0.5 liters/min and heated to 45°C over 30 minutes. The nitrogen purge was increased to 2 liters/min and 389 g (3.93 moles) gaseous phosgene was added at a rate to maintain a reaction mixture temperature of 50°-65°C over 10 minutes. The phosgene was refluxed back into the reaction vessel using a dry ice/acetone reflux condenser. After the phosgene was added, the reaction mixture was heated at 50°-65°C for 25 minutes until the solids disappeared and a clear solution resulted. The dry ice and acetone were removed from the reflux condenser and the reaction mixture was purged with nitrogen at 4 liters/min and 50°-65°C for 30 minutes. The tetrahydrofuran and excess phosgene were removed by vacuum stripping at50°-65°C down to 15 mm Hg whereupon the concentrated residue crystallized. EPO The stripped residue was dissolved in 2.8 liters anhydrous ethyl acetate and the cloudy mixture vacuum filtered to remove insoluble solids. Anhydrous hexanes (5.5 liters) were added gradually with stirring to the filtrate to crystallize the product. The product slurry was stirred for 30 minutes and refrigerated at 5°C overnight. The product was isolated by vacuum filtration under a nitrogen blanket, washed with a 0.93 liter solution of 3:1 , hexanes.ethyl acetate and with 1.4 liters hexanes, dried in the funnel by pulling vacuum on it for 30 minutes while maintaining a positive nitrogen purge and vacuum dried at room temperature to a constant weight. After drying, 461 g (89.2% yield) L-glutamic acid N-carboxyanhydride, γ-benzyl ester were produced with a melting point of92°-94°C and a chloride content of 0.022%. | 89.2% |
| With phosgene In tetrahydrofuran; toluene for 8h; Ambient temperature; | 88.3% |
| Multi-step reaction with 2 steps 1: aqueous KHCO3 2: PCl5 | |
| With bis(trichloromethyl) carbonate; α-pinene In ethyl acetate at 105℃; |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H317: May cause an allergic skin reaction [Warning Sensitization, Skin] H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Not dangerous goods |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under 2-8 °C and away from light for long term |
| Shelf Life | 1 year |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 263.25 |
| logP | 1.674 |
| HBA | 6 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 81.7 |
| Rotatable Bond (RotB) | 6 |
| Matching Veber Rules | 2 |
| Use Pattern |
| H-GLU(OBZL)-NCA CAS#: 3190-71-4 is an intermediate. |
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