4-Amino-3-(trifluoromethyl)benzoic acid → 1-[2-(4-Amino-3-trifluoromethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 2363405Notes

Reaction equation

HRID 2363405 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[O:15]=[C:16]1[O:20][CH:19]([O:21][CH2:22][CH2:23][C:24]2C=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]([NH:30][C:31]([CH:33]2[CH2:37][CH2:36][CH2:35][N:34]2[C:38](=[O:52])[CH:39]([NH:41]C(=O)C2C=CC(N)=C(Cl)C=2)[CH3:40])=[O:32])[CH2:17]1>>[CH2:22]([O:21][CH:19]1[CH:18]([NH:30][C:31]([CH:33]2[CH2:37][CH2:36][CH2:35][N:34]2[C:38](=[O:52])[CH:39]([NH:41][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=2)[CH3:40])=[O:32])[CH2:17][C:16](=[O:15])[O:20]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 32542864-Amino-3-(trifluoromethyl)benzoic acidHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide

Product 1

HCID 229775131-[2-(4-Amino-3-trifluoromethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 48%

Procedure

Prepared from {2-[2-(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbmoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester and 4-amino-3-trifluoromethyl-benzoic acid according to the procedure used to prepare 98a to afford 56 mg of title compound (48% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.20-1.55 (m, 3H), 1.75-2.50 (m, 4H), 2.50-3.10 (m, 2H), 3.50-4.00 (m, 2H), 4.30-5.00 (m, 5H), 5.42 (s, 0.4H), 5.51 (s, 0.2H), 5.62 (d, 0.3H), 5.78 (d, 0.1H), 6.84 (d, 1H), 7.20-8.15 (m, 7H). Analytical HPLC: 14.90, 15.20 min. LC-MS (ES+): m/e=563.2 (M+H+).

Sources & evidence

ORD record
ord-91f799f4761a46b0b73c47567b961820
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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