Sodium hydride → 3-amino-5-t-butoxycarbonylmethyl-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719129Notes

Reaction equation

Br.[NH2:2][CH:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][CH:4]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CN(C)C=O>[NH2:2][CH:3]1[C:9](=[O:10])[N:8]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][CH:4]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4.8 g of 3-amino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide was dissolved in 80 ml of N,N-dimethylformamide. After the addition of 1.2 g of sodium hydride (in the form of a 60% suspension in oil), the resulting mixture was stirred at 50° C. for an hour. Then, a solution of 2.7 g of t-butyl bromoacetate in 10 ml of N,N-dimethylformamide was added and the mixture was stirred at 50° C. for an additional hour. After the solvent was distilled off under reduced pressure, hexane was added to the residue so as to cause crystallization. The product was separated by filtration and washed with ether, with water and then with ether to obtain 4.0 g of the desired compound. This compound had a melting point of 178°-180° C.

Workup

stirringthe mixture was stirred at 50° C. for an additional hour
distillationAfter the solvent was distilled off under reduced pressure, hexane
additionwas added to the residue so as
customcrystallization
customThe product was separated by filtration
washwashed with ether, with water

Sources & evidence

ORD record: ord-58b030e710f74c0fab85e89c265b4261
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539150

Reaction notes

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