Methanesulfonyl chloride → 1-Tert-butoxycarbonylamino-2-(2-methanesulfonyloxyethyl)cyclopropanecarboxylic acid methyl ester

HRID 2405813Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH:6]1[CH2:8][CH2:9][OH:10])=[O:4].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH:6]1[CH2:8][CH2:9][O:10][S:20]([CH3:19])(=[O:22])=[O:21])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

1-tert-Butoxycarbonylamino-2-(2-hydroxyethyl)-cyclopropanecarboxylic acid methyl ester (0.500 g, 1.93 mmol, from Example 104) was diluted in 8 mL DCM and cooled to 0° C. under an Ar atmosphere. TEA (0.54 mL, 3.9 mmol) and methanesulfonyl chloride (0.30 mL, 3.9 mmol) were added sequentially. After 2.5 h, the solvent was removed in vacuo and the residue 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 to 50% Hex/EA) to produce 1-tert-butoxycarbonylamino-2-(2-methanesulfonyloxyethyl)cyclopropanecarboxylic acid methyl ester (0.55 g, 84%). LCMS found 360.1 [M+Na]+.

Workup

customthe solvent was removed in vacuo
extractionThe aqueous layer was extracted with 3×10 mL EtOAc
washThe combined organics were washed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentration in vacuo
customthe residue was purified by column chromatography on SiO2 (0 to 50% Hex/EA)

Sources & evidence

ORD record: ord-de5d82ac96ca436caa7c6c2a67f89645
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809267B2

Reaction notes

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