Methanol → 1309959-07-6

HRID 1027580Notes

Reaction equation

HRID 1027580 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([NH:13]S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:10][O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([NH2:13])[CH2:10][O:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 67246875HCID 67246875, compound

Product 1

HCID 672484091309959-07-6Yield 96.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(2-Nitro-benzenesulfonylamino)-isoxazolidine-2-carboxylic acid tert-butyl ester (694 mg, 1.86 mmol) and PhSH (0.142 ml, 1.1 equiv) in MeCN (10 ml) under argon at room temperature was treated with K2CO3 (386 mg, 1.5 equiv). The reaction mixture turned bright yellow. The reaction was left to stir overnight. As TLC indicated complete consumption of starting material, volatiles were removed in vacuo. Flash column chromatography eluting with dichloromethane:methanol (10/0 then 9/1) afforded 336 mg of the title amine (1.8 mmol, 96%). 1H-NMR (CDCl3, 400 MHz): 4.03-3.92 (m, 3H), 3.89-3.76 (m, 1H), 3.70 (dd, 1H), 3.37 (dd, 1H), 1.51 (s, 9H).

Workup

  1. waitThe reaction was left
  2. customconsumption of starting material, volatiles
  3. customwere removed in vacuo
  4. washFlash column chromatography eluting with dichloromethane

Sources & evidence

ORD record
ord-677367f1fc6741c6b071f1b868832556
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

Loading…