Water → (2-Benzyloxy-4-phenoxyphenylamino)acetic acid methyl ester

HRID 1642625Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[NH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].O>CN(C=O)C>[CH3:34][O:33][C:31](=[O:32])[CH2:30][NH:22][C:10]1[CH:11]=[CH:12][C:13]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-benzyloxy-4-phenoxyphenylamine (400 mg, 1.37 mmol) and K2CO3 (284 mg, 2.05 mmol) in DMF (5 mL) is added methyl bromoacetate (231 mg, 1.51 mmol). The mixture is stirred at 60° C. for 90 min., then an additional methyl bromoacetate (50 mg) is added and the mixture is stirred at 60° C. for 1 h. The mixture is allowed to cool to ambient temperature, then poured into water and extracted into EtOAc. The organic phase is washed with water (3×), saturated NaCl (1×) and dried over Na2SO4. The solvent is removed under reduced pressure to afford (2-benzyloxy-4-phenoxyphenylamino)acetic acid methyl ester. This is used directly in the next step.

Workup

stirringthe mixture is stirred at 60° C. for 1 h
temperatureto cool to ambient temperature
extractionextracted into EtOAc
washThe organic phase is washed with water (3×), saturated NaCl (1×)
dry with materialdried over Na2SO4
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-0495963b32564c73818fd5f47ec72405
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119666B2

Reaction notes

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