Methanol → 1-Tert-butoxycarbonylamino-2-(2-methanesulfonylethyl)-cyclopropanecarboxylic acid methyl ester

HRID 2405815Notes

Reaction equation

HRID 2405815 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH:6]1[CH2:8][CH2:9]SC)=[O:4].O[O:21][S:22]([O-:24])=O.[K+].[CH3:26]O>O>[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:7][CH:6]1[CH2:8][CH2:9][S:22]([CH3:26])(=[O:24])=[O:21])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 686167901-Tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)cyclopropanecarboxylic acid methyl ester

Product 1

HCID 686187851-Tert-butoxycarbonylamino-2-(2-methanesulfonylethyl)-cyclopropanecarboxylic acid methyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)-cyclopropanecarboxylic acid methyl ester (0.63 g, 2.2 mmol) in 10 mL MeOH was added slowly to a suspension of Oxone (2.0 g, 3.3 mmol) in 10 mL H2O at rt. After 2 h at it, the solvent was removed in vacuo and the residue was taken up in EtOAc and H2O (15 mL each). The aqueous layer was extracted with 3×10 mL EtOAc. The combined organics were washed with brine and dried over anhydrous MgSO4. Following concentration in vacuo, the residue was purified by column chromatography on SiO2 (0→65% EtOAc/hexanes) to produce 1-tert-butoxycarbonylamino-2-(2-methanesulfonylethyl)-cyclopropanecarboxylic acid methyl ester (0.50 g, 71%) as a colorless film. LCMS found 222.0 [(M-Boc)+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe aqueous layer was extracted with 3×10 mL EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentration in vacuo
  6. customthe residue was purified by column chromatography on SiO2 (0→65% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cbdbaa1bd3784e6d9a4655d701d357d6
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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