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

HRID 1715171Notes

Reaction equation

HRID 1715171 reaction equation
Br.C1(COC(=O)[NH:11][CH:12]([CH2:18][C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:13]([OH:17])[C:14]([NH2:16])=[O:15])C=CC=CC=1>C(O)(=O)C>[NH2:11][CH:12]([CH2:18][C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH:13]([OH:17])[C:14]([NH2:16])=[O:15]

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-44d0189bf93a47d4ad601bf92405613a
Source dataset
uspto-grants-2010_09
Patent number
US07799809B2

Reaction notes

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