Triethylamine → 2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:5].C(N(CC)CC)C.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:31](=[O:32])[CH2:30][O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:9][CH:8]=1)[CH3:5]Participants
5
Procedure
To a mixture of 2-(4-aminophenoxy)-propionic acid methyl ester 10 (20 grams, 102.5 mmol) and triethylamine (23 ml, 165 mmol) in acetone (120 ml) at 0° C. was added dropwise benzyloxy acetyl chloride (28 g, 152 mmol) followed by stirring at room temp for 12 hours. The solids were filtered off, acetone distilled off, and water (100 ml) added. Crude 51 was extracted into chloroform, washed with 5% sodium bicarbonate (2×100 ml) and water (200 ml), then dried over sodium sulphate and distilled. Crude 51 was purified by column chromatography on silica gel using benzene as eluant to get pure 51 (21 g, 59.8%) as a light brown powder with an m.p. between 67-70° C.
Workup
- filtrationThe solids were filtered off
- distillationacetone distilled off
- additionwater (100 ml) added
- extractionCrude 51 was extracted into chloroform
- washwashed with 5% sodium bicarbonate (2×100 ml) and water (200 ml)
- dry with materialdried over sodium sulphate
- distillationdistilled
- customCrude 51 was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-17cabf317c7e441ba1c8ff16e9897f35
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143325B2
Reaction notes
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