Hydrochloric Acid → (S)-2-amino-1-(3,3-difluoro-azetidin-1-yl)-3-methyl-pentan-1-one hydrochloride

Reaction equation

[ClH:1].[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.C([NH:15][C@H:16]([C:21](O)=[O:22])[C@H:17]([CH2:19][CH3:20])[CH3:18])(OC(C)(C)C)=O.Cl>>[ClH:1].[NH2:15][C@@H:16]([CH:17]([CH3:18])[CH2:19][CH3:20])[C:21]([N:5]1[CH2:6][C:3]([F:7])([F:2])[CH2:4]1)=[O:22]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 2724762tert-Butoxycarbonyl-L-isoleucine

HCID 27582473,3-Difluoroazetidine hydrochloride

Product 1

HCID 69713143(S)-2-amino-1-(3,3-difluoro-azetidin-1-yl)-3-methyl-pentan-1-one hydrochloride

Procedure

(S)-2-amino-1-(3,3-difluoro-azetidin-1-yl)-3-methyl-pentan-1-one hydrochloride was prepared by coupling 3,3-difluoro-azetidine hydrochloride (WO 0047582) with Boc-(L)-isoleucine followed by HCl deprotection as analogously described in Example 1 (mp 195° C. dec.).

Sources & evidence

ORD record: ord-8454b09149134b8bb6599e0436bd96ab
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710040B1

Reaction notes

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