(4-Isocyanato-phenoxy)-acetic acid methyl ester → {4-[2-(4-Methoxycarbonylmethoxy-phenylcarbamoyloxy)-ethoxycarbonylamino]-phenoxy}-acetic acid methyl ester
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To [4-(2-Hydroxyethoxycarbonylamino)-phenoxy]-acetic acid methyl ester 5 (1 g, 3.72 mmol) in toluene (10 ml) was added (4-Isocyanatophenoxy)-acetic acid methyl ester 4 (0.8 gram, 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 6 was extracted into chloroform, dried over sodium sulphate, distilled and purified by column chromatography on silica gel using chloroform as eluant to g pure 6 (1 gram, 56.5%) as a white fluffy powder.
Workup
- distillationToluene was distilled off
- additionwater (10 ml) was added
- extractionCrude 6 was extracted into chloroform
- dry with materialdried over sodium sulphate
- distillationdistilled
- custompurified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-365cd63a16fb4ee085e3952c0d9ddfcb
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772352B2
Reaction notes
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