6-(4-Isocyanatophenoxy)-hexanoic acid methyl ester → 6-(4-{2-[4-(5-Methoxycarbonyl-pentyloxy)-phenylcarbamoyloxy]-ethoxycarbonylamino}-phenoxy)-hexanoic acid methyl ester

HRID 1957844Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([O:19][CH2:20][CH2:21][OH:22])=[O:18])=[CH:12][CH:11]=1.[CH3:24][O:25][C:26](=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[O:41])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]([O:19][CH2:20][CH2:21][O:22][C:40](=[O:41])[NH:39][C:36]2[CH:35]=[CH:34][C:33]([O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:26]([O:25][CH3:24])=[O:42])=[CH:38][CH:37]=2)=[O:18])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 6-[4-(2-Hydroxyethoxycarbonylamino)phenoxy]hexanoic acid methyl ester 37 (5 g, 15.38 mmol) in toluene (50 ml) was added 6-(4-Isocyanatophenoxy)hexanoic acid methyl ester 36 (4 g, 15.2 mmol) at room temperature and heated to 60° C. for 2 hours. Toluene was distilled off and water (50 ml) was added. The solid was filtered and dried to give crude 38, which was purified by column chromatography on silica gel using chloroform as eluant to get pure 38 (8.5 g, 94%) as a white powder. M.p: 118-120.5° C.

Workup

distillationToluene was distilled off
additionwater (50 ml) was added
filtrationThe solid was filtered
customdried
customto give crude 38, which
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-629d7deee69740c19b82f28d4ed1ae96
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08409559B2

Reaction notes

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