(4-Isocyanato-phenoxy)-acetic acid methyl ester → {4-[2-(4-Methoxycarbonylmethoxy-phenylcarbamoyloxy)-ethoxycarbonylamino]-phenoxy}-acetic acid methyl ester

HRID 638721Notes

Reaction equation

HRID 638721 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][CH2:17][OH:18])=[O:14])=[CH:8][CH:7]=1.[CH3:20][O:21][C:22](=[O:34])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([O:15][CH2:16][CH2:17][O:18][C:32](=[O:33])[NH:31][C:28]2[CH:27]=[CH:26][C:25]([O:24][CH2:23][C:22]([O:21][CH3:20])=[O:34])=[CH:30][CH:29]=2)=[O:14])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 18918618(4-Isocyanato-phenoxy)-acetic acid methyl esterHCID 49764368[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl ester

Product 1

HCID 59253986{4-[2-(4-Methoxycarbonylmethoxy-phenylcarbamoyloxy)-ethoxycarbonylamino]-phenoxy}-acetic acid methyl esterYield 56.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To [4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl ester 29 (1 g, 3.72 mmol) in toluene (10 ml) was added (4-Isocyanato-phenoxy)-acetic acid methyl ester 28 (0.8 g, 3.8 mmol) at room temperature and heated to 50° C. for 20 hours. Toluene was distilled off and water (10 ml) was added. Crude 30 was extracted into chloroform, dried over sodium sulphate, distilled and purified by column chromatography on silica gel using chloroform as eluant to get pure 30 (1 g, 56.5%) as a white fluffy powder.

Workup

  1. distillationToluene was distilled off
  2. additionwater (10 ml) was added
  3. extractionCrude 30 was extracted into chloroform
  4. dry with materialdried over sodium sulphate
  5. distillationdistilled
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-79436a047415479ca8505657f7179884
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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