Hydrochloric Acid → HCID 66954873, compound

HRID 2190955Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH2:13][C:14]([F:20])([F:19])[CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.[ClH:21]>>[ClH:21].[NH2:8][C@@H:9]([CH2:13][C:14]([F:19])([F:20])[CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:10]([OH:12])=[O:11]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 53348251HCID 53348251, compound

Product 1

HCID 66954873HCID 66954873, compound

Procedure

A preferred aspect of the invention is a process for the preparation of (S)-methyl 2-amino-5-cyclopropyl-4,4-difluoropentanoate hydrochloride, which process comprises: (a) reacting (R,S)-ethyl 2-(tert-butoxycarbonylamino)-5-cyclopropyl-4,4-difluoropentanoate with Alcalase to give a mixture of (R)-ethyl 2-(tert-butoxycarbonylamino)-5-cyclopropyl-4,4-difluoropentanoate and (S)-2-(tert-butoxycarbonylamino)-5-cyclopropyl-4,4-difluoropentanoic acid; (b) isolating the (S)-2-(tert-butoxycarbonylamino)-5-cyclopropyl-4,4-difluoropentanoic acid; (c) deprotecting the (S)-2-(tert-butoxycarbonylamino)-5-cyclopropyl-4,4-difluoropentanoic acid with hydrochloric acid to give (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid hydrochloride; and (d) treating the (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid hydrochloride with methanol.

Sources & evidence

ORD record: ord-c0d8e693cd1d48a2868f5b74f9e247ff
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324417B2

Reaction notes

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