Hydrogen Bromide → HCID 18648268, compound

HRID 466858Notes

Reaction equation

HRID 466858 reaction equation
C(OC([NH:11][C@@H:12]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:13]([OH:27])[CH2:14][N:15]1[C@H:19]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][S:17][CH2:16]1)=O)C1C=CC=CC=1.[BrH:35]>C(O)(=O)C.C(OCC)C>[BrH:35].[BrH:35].[NH2:11][C@@H:12]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C@H:13]([OH:27])[CH2:14][N:15]1[C@H:19]([C:20]([NH:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH2:18][S:17][CH2:16]1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 573244103-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide

Product 1

HCID 18648268HCID 18648268, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2 g of 3-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide and 4.1 ml of 32% (w/w) hydrogen bromide in glacial acetic acid was stirred at room temperature for 1 hour. The resulting solution was diluted with anhydrous diethyl ether and the precipitated product was rapidly filtered off and washed with fresh diethyl ether. There were obtained 2.01 g of 3-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide dihydrobromide as a white solid; 1H NMR (300 MHz): δ (D2O) 1.37 (9H, s), 3.0 (2H, m), 3.09 (2H, dq), 3.29 (2H, d), 3.85 (2H, m), 4.16 (1H, m), 4.3 (2H, q) and 7.42 (5H, m) ppm.

Workup

  1. filtrationthe precipitated product was rapidly filtered off
  2. washwashed with fresh diethyl ether

Sources & evidence

ORD record
ord-c7291a3b69334947942eea4282d9d90f
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

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