Hydrogen chloride-ethyl acetate → (1R,2S)-2-amino-N-[(3-hydroxypropyl)sulfonyl]cyclopentane carboxamide hydrochloride

HRID 1662069Notes

Reaction equation

HRID 1662069 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([NH:16][S:17]([CH2:20][CH2:21][CH2:22]CC(O)=O)(=[O:19])=[O:18])=[O:15])=O)(C)(C)C.[ClH:27].C(OCC)(=[O:30])C>CO>[ClH:27].[NH2:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([NH:16][S:17]([CH2:20][CH2:21][CH2:22][OH:30])(=[O:18])=[O:19])=[O:15]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 674291603-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid

Product 1

HCID 67429041(1R,2S)-2-amino-N-[(3-hydroxypropyl)sulfonyl]cyclopentane carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid (1.2 g) and methanol (12 ml) was added a 4 M hydrogen chloride/ethyl acetate solution (6.0 ml) under ice-cooling, followed by stirring at room temperature over one night. The reaction mixture was concentrated under reduced pressure to obtain (1R,2S)-2-amino-N-[(3-hydroxypropyl)sulfonyl]cyclopentane carboxamide hydrochloride (1.1 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7329753a7f544dfadd68abc96c83f23
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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