Hydrogen Bromide → 3-Amino-2-hydroxy-4-(2-thienyl)butanamide

HRID 12435Notes

Reaction equation

HRID 12435 reaction equation
Br.[NH2:2][C:3](=[O:24])[CH:4]([OH:23])[CH:5]([NH:12]C(=O)OCC1C=CC=CC=1)[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1>C(O)(=O)C>[NH2:12][CH:5]([CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH:4]([OH:23])[C:3]([NH2:2])=[O:24]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86623368HCID 86623368, compound

Product 1

HCID 667184663-Amino-2-hydroxy-4-(2-thienyl)butanamideYield 131.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

70 ml of 30% HBr in glacial acetic acid were added to 11 g of phenylmethyl [3-amino-2-hydroxy-3-oxo-1-(2-thienylmethyl)propyl]carbamate (29.66 mmol) in 30 ml of glacial acetic acid. After about 2 hours, the mixture was concentrated and the resulting residue was stirred firstly with cyclohexane and then with dichloromethane. 7.8 g of the title compound were obtained as hydrobromide.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-4c437eb2a50340bdb7d8605ab5fe4e4d
Source dataset
uspto-grants-2010_06
Patent number
US07728012B2

Reaction notes

Loading…