1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide → 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900618Notes

Reaction equation

HRID 900618 reaction equation
C(OC(C1CCCN1C(=O)C(NC(=O)C1C=CC(N)=C(Cl)C=1)C)=O)(C)(C)C.[O:28]=[C:29]1[O:33][CH:32]([O:34][CH2:35][CH2:36][C:37]2C=CC=[CH:39][CH:38]=2)[CH:31]([NH:43][C:44]([CH:46]2[CH2:50][CH2:49][CH2:48][N:47]2[C:51](=[O:65])[CH:52]([NH:54][C:55](=[O:64])[C:56]2[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([Cl:63])[CH:57]=2)[CH3:53])=[O:45])[CH2:30]1>>[CH:35]1([O:34][CH:32]2[CH:31]([NH:43][C:44]([CH:46]3[CH2:50][CH2:49][CH2:48][N:47]3[C:51](=[O:65])[CH:52]([NH:54][C:55](=[O:64])[C:56]3[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([Cl:63])[CH:57]=3)[CH3:53])=[O:45])[CH2:30][C:29](=[O:28])[O:33]2)[CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amideHCID 536934251-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 229775031-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 59%

Procedure

Prepared from 97a and syn-(2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford the title compound as an off-white solid (0.19 g, 59% yield). 1H-NMR (500 MHz, CDCl3) δ 1.2-2.4 (m, 15H), 2.4-3.1 (m, 2H), 3.6-3.9 (m, 2H), 4.2-4.4 (m, 2H), 4.5-5.0 (m, 4H), 5.40 (d, J=5.0 Hz, 0.35H), 5.55 (d, J=5.0 Hz, 0.65H), 6.8-8.2 (m, 5H) ppm. Analytical HPLC (C18column) 14.065 min. LC-MS (ES+): m/e=507 (M+H).

Sources & evidence

ORD record
ord-6de5a12e07cc4f27a303c5e7fdd559f7
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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