4-Acetamido-3-chlorobenzoic acid → 1-[2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 2363382Notes

Reaction equation

HRID 2363382 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[Cl:14])(=[O:3])[CH3:2].[C:15]([O:19][C:20]([CH:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:27](=[O:41])[CH:28]([NH:30]C(=O)C1C=CC(N)=C(Cl)C=1)[CH3:29])=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[C:15]([O:19][C:20]([CH:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:27](=[O:41])[CH:28]([NH:30][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([Cl:14])[CH:7]=1)[CH3:29])=[O:21])([CH3:17])([CH3:16])[CH3:18]

Participants

3

Reactant 2

HCID 6809514-Acetamido-3-chlorobenzoic acidHCID 536934251-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 536986101-[2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl esterYield 77%

Procedure

Prepared from 95 and 4-acetylamino-3-chlorobenzoic acid according to the method used for 96a to afford the title compound as a white solid (9.18 g, 77% yield) 1H-NMR (500 MHz, CD3OD) δ 1.30-1.62 (m, 12H), 1.85-2.16 (m, 3H), 2.16-2.44 (m, 1H), 2.27 (s, 3H), 3.47-3.83 (m, 2H), 4.34-4.54 (m, 1H), 4.89 (m, 1H), 7.27-7.39 (m, 1H), 7.59-7.71 (m, 2H), 7.83-7.97 (m, 1H), 8.47 (d, 1H). Analytical HPLC 9.43 min.

Sources & evidence

ORD record
ord-b3932b1228ef43dfa229b1067819df51
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

Loading…