Trifluoroacetic acid → (1S,2R)-1-amino-2-phenyl-N-propylcyclopropanecarboxamide trifluoroacetate

HRID 882579Notes

Reaction equation

C(OC([NH:8][C@@:9]1([C:18]([OH:20])=O)[CH2:11][C@@H:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.[CH2:21]([NH2:24])[CH2:22][CH3:23].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52]>>[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52].[NH2:8][C@@:9]1([C:18]([NH:24][CH2:21][CH2:22][CH3:23])=[O:20])[CH2:11][C@@H:10]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 7852Propylamine

HCID 7009512(1S,2R)-N-Boc-1-amino-2-phenylcyclopropanecarboxylic acid

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71294530(1S,2R)-1-amino-2-phenyl-N-propylcyclopropanecarboxamide trifluoroacetateYield 85%

Procedure

The title compound was prepared by coupling commercially available (1S,2R)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylic acid with n-propylamine in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) and subsequent Boc detachment with trifluoroacetic acid (yield: 85% of theory over both stages).

Sources & evidence

ORD record: ord-9e117ccc27b94790bb801a036ff93700
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08992932B2

Reaction notes

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