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

HRID 1957841
Notes
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Reaction equation

HRID 1957841 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 497643632-(4-Isocyanato-phenoxy)-propionic acid methyl esterHCID 592539572-[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-propionic acid methyl ester

Product 1

HCID 592539282-(4-{2-[4-(1-Methoxycarbonyl-ethoxy)-phenylcarbamoyloxy]-ethoxycarbonylamino}-phenoxy)-propionic acid methyl esterYield 61.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. distillationToluene was distilled off
  2. additionwater (50 ml) was added
  3. filtrationThe solids were filtered
  4. customdried
  5. customto give crude 34, which
  6. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes