(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl ester → 1-[2-(4-Methoxy-3,5-dimethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900607Notes

Reaction equation

HRID 900607 reaction equation
C(O[C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:29])[CH:14]([NH:16][C:17](=[O:28])[C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([O:25][CH3:26])=[C:20]([CH3:27])[CH:19]=1)[CH3:15])=[O:7])(C)(C)C.C(OC(=O)[NH:35][CH:36]1[CH2:40][C:39](=[O:41])[O:38][CH:37]1[O:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47]C=1)C=C.O=C1OC(OCCC2C=CC=CC=2)C(NC(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)C1>>[CH2:43]([O:42][CH:37]1[CH:36]([NH:35][C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13](=[O:29])[CH:14]([NH:16][C:17](=[O:28])[C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([O:25][CH3:26])=[C:20]([CH3:27])[CH:19]=2)[CH3:15])=[O:7])[CH2:40][C:39](=[O:41])[O:38]1)[C:44]1[CH:45]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

4

Reactant 3

HCID 18465651(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl esterHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amideHCID 539406531-[2-(4-Methoxy-3,5-dimethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 229777771-[2-(4-Methoxy-3,5-dimethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 71%

Procedure

Prepared from 1-[2-(4-methoxy-3,5-dimethyl-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester and syn-(2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester (40) according to the procedure used to prepare 98a to afford 406 mg (yield 71%) of the title compound. 1H-NMR (500 MHz, CDCl3): δ 1.09 (d, 0.6H), 1.35 (m, 2.4H), 1.90-2.20 (m, 3H), 2.22-2.50 (m, 10H), 2.84-2.90 (m, H), 3.52-3.62 (m, 1.6H), 3.65-3.80 (m, 3.4H), 4.10-4.40 (m, H), 4.50-4.75 (m, 3H), 4.82-4.95 (m, 2H), 5.54 (d, 0.8H), 5.80 (d, 0.2H), 6.87 (d, H), 7.10-7.40 (m, 6H), 7.45 (s, 2H); retention time on analytical HPLC: 16.71 min1; LC-MS: m/z=538 (M+H+).

Sources & evidence

ORD record
ord-cbd08786672649488ec75ff9cba34315
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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