Benzenepropanol → (5-Oxo-2-(3-phenyl-propoxy)-tetrahydro-furan-3-yl)-carbamic acid allyl ester

HRID 900600Notes

Reaction equation

HRID 900600 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][CH:8]([NH:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH2:9][OH:10])(C)(C)C.C(OC(=O)NC1CC(=O)OC1OCCC1C=CC=CC=1)C=C.[C:41]1([CH2:47][CH2:48][CH2:49]O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:15]([O:14][C:12](=[O:13])[NH:11][CH:8]1[CH2:7][C:6](=[O:5])[O:18][CH:9]1[O:10][CH2:49][CH2:48][CH2:47][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:16]=[CH2:17]

Participants

4

Reactant 3

HCID 31234BenzenepropanolHCID 18465651(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl esterHCID 542397063-Allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester

Product 1

HCID 54014313(5-Oxo-2-(3-phenyl-propoxy)-tetrahydro-furan-3-yl)-carbamic acid allyl esterYield 32%

Procedure

Prepared from 3-allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester as described for compound 40 using 3-phenylpropanol to afford 1.15 grams (32% yield) of the title compound as a colorless oil. 1H-NMR (500 MHz, CDCl3) δ 1.82-2.05 (m, 2H), 2.38 (dd, 1H), 2.68 (m, 2H), 2.82 (dd, 1H), 3.55-3.65 (m, 1H), 3.82-3.92 (m, 1H), 4.48-4.72 (m, 3H), 5.12-5.59 (m, 3H), 5.82-6.03 (m, 1H), 7.11-7.45 (m, 5H). Analytical HPLC: 9.08 min. LC-MS (ES+): m/e=320.2 (M+H+).

Sources & evidence

ORD record
ord-3eef8e75d94443d08096238972e7d184
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

Loading…