(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid → HCID 90802328, compound

HRID 1863969Notes

Reaction equation

HRID 1863969 reaction equation
[NH:1]([C:3]1[N:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=[C:7]2[CH:6]=[CH:5][N:4]=1)[NH2:2].[C:16]([O:20][C:21]([NH:23][C@H:24]([CH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[F:38])[CH2:25][C:26](O)=[O:27])=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][C:21](=[O:22])[NH:23][C@H:24]([CH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[F:38])[CH2:25][C:26](=[O:27])[NH:2][NH:1][C:3]1[N:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=[C:7]2[CH:6]=[CH:5][N:4]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

3

Reactant 2

HCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid2×HCID 57973806HCID 57973806, compound2×

Product 1

HCID 90802328HCID 90802328, compound

Procedure

By the procedure of Example 9, Step A, 5-hydrazino-2-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidine (Intermediate 42) was acylated with (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (Intermediate 3). Purification by flash chromatography on silica gel (1-5% methanol in dichloromethane) afforded the title compound as a light tan solid, mp 159-161° C. LC-MS 534 (M+1).

Workup

  1. customPurification by flash chromatography on silica gel (1-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a1b8e2fe782548ffac9196442d2b6399
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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