Ammonia → 3-(Tert-butylsulfinylamino)-3-cyclopropyl-butanamide

HRID 1480324Notes

Reaction equation

HRID 1480324 reaction equation
[CH:1]1([C:4]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])([CH3:11])[CH2:5][C:6](OCC)=[O:7])[CH2:3][CH2:2]1.CO.[NH3:21]>>[C:15]([S:13]([NH:12][C:4]([CH:1]1[CH2:3][CH2:2]1)([CH3:11])[CH2:5][C:6]([NH2:21])=[O:7])=[O:14])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 90204431Ethyl 3-(tert-butylsulfinylamino)-3-cyclopropyl-butanoate

Product 1

HCID 902035133-(Tert-butylsulfinylamino)-3-cyclopropyl-butanamideYield 15%

Conditions

Temperature
45 °C

Procedure

A solution of ethyl 3-cyclopropyl-3-(1,1-dimethylethylsulfinamido)butanoate (1.16 g, 4.21 mmol) in ammonia 7N in methanol (20 ml, 140 mmol) in a microwave sealed tube was stirred at 45° C. overnight. The volatiles were removed in vacuo and the residue was directly purified by flash chromatography on silica eluting with a gradient of dichloromethane/methanol to yield the title compound (155 mg, 15%); MS (ESI, m/z): 247.2 (M+H+).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was directly purified by flash chromatography on silica eluting with a gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-5e6c8f2e30654fd0a0f6fd5f3a827e8a
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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