Methanol → HCID 67247073, compound

HRID 1027579Notes

Reaction equation

HRID 1027579 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([N:12]1[CH2:16][CH:15]([NH:17]S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:14][O:13]1)=[O:11].C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO>C(#N)C>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([N:12]1[CH2:16][CH:15]([NH2:17])[CH2:14][O:13]1)=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 67248086HCID 67248086, compound

Product 1

HCID 67247073HCID 67247073, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-[4-(2-Nitro-benzenesulfonylamino)-isoxazolidine-2-carbonyl]-benzoic acid methyl ester (200 mg, 0.46 mmol) and PhSH (0.035 ml, 1.1 equiv) in acetonitrile (2.3 ml) under argon at rt was treated with K2CO3 (95 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 (9/1) afforded 85 mg of the expected amine (0.34 mmol, 74%). LCMS (Method E) 0.55 and 1.41 min, M+H 251. 1H-NMR (CDCl3, 400 MHz): 7.95 (d, 1H), 7.63-7.52 (m, 1H), 7.51-7.36 (m, 2H), 4.17-3.92 (m, 3H), 3.87 (s, 3H), 3.80-3.55 (m, 2H), 2.04-1.75 (m, 2H).

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-ca20940dabf64fbab585bccbd25c5f50
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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