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-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900593Notes

Reaction equation

HRID 900593 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([O:7][CH2:8]CC2C=CC=CC=2)[CH:4]([NH:16][C:17]([CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:24](=[O:38])[CH:25]([NH:27][C:28](=[O:37])[C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[C:31]([Cl:36])[CH:30]=2)[CH3:26])=[O:18])[CH2:3]1.N(C(OC[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=O)[C@H](C(O)=O)C.C1CN[C@@H](C(O)=O)C1>>[CH2:8]([O:7][CH:5]1[CH:4]([NH:16][C:17]([CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:24](=[O:38])[CH:25]([NH:27][C:28](=[O:37])[C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[C:31]([Cl:36])[CH:30]=2)[CH3:26])=[O:18])[CH2:3][C:2](=[O:1])[O:6]1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=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 131723793Cbz-Ala D-pro-OH

Product 1

HCID 229774991-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 69%

Procedure

Prepared according to the procedure used to prepare 98a using Cbz-Ala-D-pro-OH to afford 230 mg of title compound (69% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.30 (d, 1.2H), 1.45 (d, 1.8H), 1.62-2.40 (m, 4H), 2.40-3.10 (m, 2H), 3.30-3.97 (m, 2H), 4.33-4.95 (m, 5H), 5.30 (s, 0.5H), 5.68 (d, 0.5H), 6.80 (d, 1H), 7.25-7.95 (m, 7H). Analytical HPLC: 11.56, 11.91 min. LC-MS (ES+): m/e=529.2 (M+H+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2d78043db45a482da60dce9b0210171a
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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