2-(4-Isocyanato-phenoxy)-propionic acid methyl ester → 2-(4-{2-[4-(1-Methoxycarbonyl-ethoxy)-phenylcarbamoyloxy]-ethoxycarbonylamino}-phenoxy)-propionic acid methyl ester

HRID 1957841Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])=[CH:9][CH:8]=1)[CH3:5].[CH3:21][O:22][C:23](=[O:36])[CH:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1)[CH3:25]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][CH2:18][O:19][C:34](=[O:35])[NH:33][C:30]2[CH:29]=[CH:28][C:27]([O:26][CH:24]([C:23]([O:22][CH3:21])=[O:36])[CH3:25])=[CH:32][CH:31]=2)=[O:15])=[CH:9][CH:8]=1)[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To 2-[4-(2-Hydroxyethoxycarbonylamino)phenoxy]propionic acid methyl ester 33 (5 g, 17.66 mmol) in toluene (50 ml) was added 2-(4-Isocyanato-phenoxy)-propionic acid methyl ester 32 (3.9 g, 17.64 mmol) at room temperature and heated to 60° C. for 30 hours. Toluene was distilled off and water (50 ml) was added. The solids were filtered and dried to give crude 34, which was purified by column chromatography on silica gel using chloroform as eluant to get pure 34 (5.5 g, 61.8%) as a white powder. M.p: 98-100° C.

Workup

distillationToluene was distilled off
additionwater (50 ml) was added
filtrationThe solids were filtered
customdried
customto give crude 34, which
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-47a5d38b44414764b7aad2bccc8ecf14
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08409559B2

Reaction notes

Loading…