tert-Butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate → tert-Butyl 1-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluoro-benzyl)cyclopropanecarboxylate

HRID 1475660Notes

Reaction equation

HRID 1475660 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:22][C:23]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([NH:18][C:19]2[CH:20]=[C:21]([CH:33]=[CH:34][C:35]=2[F:36])[CH2:22][C:23]2([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 58136688tert-Butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylateHCID 67206916(2RS,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid

Product 1

HCID 68006903tert-Butyl 1-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluoro-benzyl)cyclopropanecarboxylate

Procedure

According to General Procedure 6, 1.2 g (4.5 mmol) of (2RS,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid and 1.3 g (4.95 mmol) of tert-butyl 1-(3-amino-4-fluorobenzyl)-cyclopropanecarboxylate gave, after purification of the crude product by flash chromatography (silica gel; mobile phase cyclohexane/ethyl acetate 20:1), 1.6 g (69% of theory) of the title compound.

Workup

  1. customgave
  2. customafter purification of the crude product by flash chromatography (silica gel; mobile phase cyclohexane/ethyl acetate 20:1), 1.6 g (69% of theory) of the title compound

Sources & evidence

ORD record
ord-940f49e2643943828a456fc720de49e4
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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