| Identification | Back Directory | [Name]
benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate | [CAS]
868540-15-2 | [Synonyms]
EOS-60551
Carfilzomib INT
Reaxys ID: 14504822
benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate
(αS)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-phenylmethyl Ester L-Phenylalanine
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-,L-Phenylalanine phenylmethyl ester
L-Phenylalanine, (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-, phenylmethyl ester
(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine phenylmethyl ester
(6S,9S,12S)-benzyl 12-benzyl-9-isobutyl-2,2-dimethyl-4,7,10-trioxo-6-phenethyl-3-oxa-5,8,11-triazatridecan-13-oate
Benzyl (2S)-2-[[(2S)-4-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoyl]amino]pentanoyl]amino]-3-phenylpropanoate | [Molecular Formula]
C37H47N3O6 | [MDL Number]
MFCD29044885 | [MOL File]
868540-15-2.mol | [Molecular Weight]
629.8 |
| Chemical Properties | Back Directory | [Melting point ]
150 - 151°C | [Boiling point ]
818.2±65.0 °C(Predicted) | [density ]
1.137±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated) | [form ]
Solid | [pka]
11.22±0.46(Predicted) | [color ]
White to Off-White | [InChIKey]
AKIABKDAWVWIHO-DPQUEHIJNA-N | [SMILES]
[C@H](C(=O)OCC1C=CC=CC=1)(NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)OC(C)(C)C)CCC1C=CC=CC=1)CC1C=CC=CC=1 |&1:0,14,22,r| |
| Hazard Information | Back Directory | [Uses]
(αS)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-phenylmethyl Ester L-Phenylalanine is used as a reagent in the preparation of peptides for inhibition of enzymes. | [Synthesis]
Example 2: Preparation of Compound of Formula VII
1. Cool a mixture of dichloromethane (90 mL) and trifluoroacetic acid (210 mL) to 2-6 °C and add the compound of Formula IV (100 g, 1 eq.) at 37 °C. Maintain the same temperature.
2. The reaction mixture was heated to 25-30 °C and stirred at this temperature for 2 hours.
3. Add dichloromethane (1.5 L) to the reaction mixture, adjust the pH to 7-8 with 25% sodium carbonate solution at 20-30 °C and stir for 20 min at the same temperature.
4. The organic layer was separated and washed sequentially with water (300 mL) and 10% sodium chloride solution (300 mL).
5. Separate the organic layer and concentrate under vacuum at less than 35°C to obtain a residue.
6. The resulting residue was dissolved in dimethylformamide (500 mL) and cooled to 2-6°C. 7.
7. HOBt (2.9 g, 0.1 eq.), PyBOP (133.5 g, 1.2 eq.), N-Boc-homophenylalanine (59.7 g, 1 eq.) and diisopropylethylamine (110.5 g, 4 eq.) were slowly added to the reaction mixture at 2-6 °C.
8. The reaction mixture was heated to 25-30 °C and stirred at this temperature for 2-3 hours.
9. After completion of the reaction, the reaction mixture was slowly poured into water (5 L) at 25-30 °C and stirred at the same temperature for 2-3 hours.
10. The precipitated solid was filtered, washed with water (500 mL) and dried to afford (αS)-α-[[tert-butoxycarbonyl]amino]phenylbutyryl-L-leucyl-L-phenylalanine benzyl ester.
Yield: 130 g; PXRD: Figure 2; DSC: heat-absorption peak at ca. 150 °C; HPLC chemical purity: 99.97%; HOBt: 0.1%, PyBOP: not detected, tris(pyrrolidinylphosphine) oxide: 0.02% by HPLC, respectively. | [References]
[1] Patent: WO2016/185450, 2016, A1. Location in patent: Page/Page column 61-62 |
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