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

HRID 2169722Notes

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-c8bc6f537fa340bda0f8b03b932169c0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE045548E1

Reaction notes

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