Dimethylformamide → HCID 54341310, compound

HRID 1284944Notes

Reaction equation

HRID 1284944 reaction equation
CN(C)C=O.[C:6]([C@@H:9]([NH:18][C@@H:19]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:23]2[CH:35]=[CH:36][CH:37]=[CH:38][C:22]=2[S:21][CH2:20]1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([OH:8])=[O:7].C(=O)(O)[O-].[Na+].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O>[CH2:44]([O:7][C:6]([C@@H:9]([NH:18][C@@H:19]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[C:23]2[CH:35]=[CH:36][CH:37]=[CH:38][C:22]=2[S:21][CH2:20]1)[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 13454584HCID 13454584, compound

Product 1

HCID 54341310HCID 54341310, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 ml of N,N-dimethylformamide, 0.3 g of tert-butyl 3(R)-[1(S)-carboxy-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate obtained in Example 43, 0.5 g of sodium bicarbonate and 0.15 g of benzyl bromide is stirred at room temperature overnight. The mixture is diluted with water (100 ml) and extracted with ethyl acetate (200 ml). The extract is washed successively with 0.1N hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.35 g of tert-butyl 3(R)-[1(S)-benzyloxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate (200 ml)
  2. washThe extract is washed successively with 0.1N hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a75644ec2c64c3e8e79c798b9944cda
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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