Acetyl chloride → HCID 70045264, compound

HRID 267166Notes

Reaction equation

HRID 267166 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[NH2:6][C@H:7]1[CH2:11][N:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C@H:9]([C:16]([NH:18][CH2:19][C@@H:20]([OH:48])[C@@H:21]([NH:29][C:30](=[O:47])[C@H:31]([CH2:43][C:44](=[O:46])[NH2:45])[NH:32][C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[CH2:8]1.C(=O)(O)[O-].[Na+]>O.CN(C)C=O>[C:1]([NH:6][C@H:7]1[CH2:11][N:10]([C:12]([CH3:14])([CH3:13])[CH3:15])[C@H:9]([C:16]([NH:18][CH2:19][C@@H:20]([OH:48])[C@@H:21]([NH:29][C:30](=[O:47])[C@H:31]([CH2:43][C:44](=[O:46])[NH2:45])[NH:32][C:33]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[CH2:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 86746295HCID 86746295, compound

Product 1

HCID 70045264HCID 70045264, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

15 mg of freshly distilled acetyl chloride were added to a solution, which was cooled to 0° C. and stirred, of 12 mg of 4(R)-amino-N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide hydrochloride and 21 mg of sodium bicarbonate in 0.5 ml of water and 0.25 ml of dimethylformamide. The mixture was stirred vigorously at 0° C. for 5 hours and then left to stand at room temperature overnight. The mixture was diluted with water and extracted with dichloromethane. The combined dichloromethane extracts were evaporated to give a gum which was purified by flash chromatography on silica gel using 20% methanol in dichloromethane for the elution. There were obtained 2 mg of 4(R)-acetylamino-N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a semi-solid; MS: m/e 639 [M+H]+.

Workup

  1. waitleft
  2. waitto stand at room temperature overnight
  3. extractionextracted with dichloromethane
  4. customThe combined dichloromethane extracts were evaporated
  5. customto give a gum which
  6. customwas purified by flash chromatography on silica gel using 20% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-70a5881e55964250b25ed93ba501e163
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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