Water → (4-t-Butoxycarbonylmethoxy-2-methylphenylamino)-acetic acid methyl ester

HRID 1592029Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].O>CN(C=O)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])=[CH:10][C:11]=1[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2.1 g (8.9 mmol) of the title B compound, (4-amino-3-methylphenoxy)-acetic acid t-butyl ester and 2.44 g (17.7 mmol) of potassium carbonate in 8 mL of DMF are added 1.76 g (11.5 mmol) of methyl bromoacetate. The mixture is stirred at 60° C. for 1 h, then allowed to cool to RT. The mixture is poured into water and extracted with EtOAc. The organic phase is washed with water and brine, and dried over anhydrous Na2SO4. The solvent is removed under reduced pressure and the residue is chromatographed using CH2Cl2 as the eluant to afford (4-t-butoxycarbonylmethoxy-2-methylphenylamino)-acetic acid methyl ester as an oil (contaminated with approx 25% of dialkylated product): 1H-NMR (CDCl3) δ 6.76-6.64 (m, 2H), 6.40 (d, J=8.46, 1H), 4.43 (s, 2H), 3.91 (s, 2H), 3.78 (s, 3H), 2.19 (s, 3H), 1.48 (s, 9H).

Workup

temperatureto cool to RT
extractionextracted with EtOAc
washThe organic phase is washed with water and brine
dry with materialdried over anhydrous Na2SO4
customThe solvent is removed under reduced pressure
customthe residue is chromatographed

Sources & evidence

ORD record: ord-63d1f5f7a5354798b1379928d4342338
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291635B2

Reaction notes

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