Water → [2-Benzyloxy-4-(7-oxo-azepan-2-ylmethyl)-phenylamino]-acetic Acid Methyl Ester

HRID 660553Notes

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]2[NH:13][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34].O>CN(C=O)C>[CH3:36][O:35][C:33](=[O:34])[CH2:32][NH:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:14])[NH:13]2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 7-(4-Amino-3-benzyloxybenzyl)-azepan-2-one (600 mg, 1.7 mmol) and potassium carbonate (345 mg, 2.5 mmol) in DMF (10 mL) is added methyl bromoacetate (383 mg, 2.5 mmol). The mixture is stirred at 60° C. for 4 h then is allowed to cool to RT. It is poured into water and extracted with EtOAc and the organic phase is washed with water (3×), brine (1×), and dried over Na2SO4. The solvent is removed under reduced pressure to afford the title compound which is used directly in the next step.

Workup

temperatureto cool to RT
extractionextracted with EtOAc
washthe organic phase is washed with water (3×), brine (1×)
dry with materialdried over Na2SO4
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-9852189954ba4ac69629b740e93d680e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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