Thiophenol → 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate

HRID 1160408Notes

Reaction equation

HRID 1160408 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][N:21]([CH2:34][CH3:35])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH2:34][CH3:35])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 595161701,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-{ethyl[(2-nitrophenyl)sulfonyl]amino}butanoate

Product 1

HCID 595162371,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The crude 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-{ethyl[(2-nitrophenyl)sulfonyl]amino}butanoate from the previous step (16.2 mmol), phenyl hydrosulfide (1.0 equiv., 1.78 g, 16.2 mmol), and K2CO3 (325 mesh, 3 equiv., 6.71 g, 48.6 mmol) in DMF (60 mL) were stirred at room temperature for 90 min. The reaction mixture was diluted with H2O (200 mL) and extracted with Et2O (3×). The organic extracts were washed with H2O, and 10% aq. Na2CO3, dried, and concentrated to give the titled product which was contaminated with the 2-nitrophenyl phenyl sulfide by-product. This contaminated product was used directly in the next step.

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe organic extracts were washed with H2O, and 10% aq. Na2CO3
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8122a2a5820c47fba3a48fc90d65b8f1
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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