Formic Acid → tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate

HRID 927200Notes

Reaction equation

HRID 927200 reaction equation
[CH:1](O)=O.[C:4](=[O:11])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[NH2:5].C([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[S:22]([CH3:25])(=[O:24])=[O:23])=O.[C:26]1([S:32]([O-:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na+]>O1CCCC1.O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([N:5]([CH2:1][S:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:34])=[O:33])[C:4](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[C:15]([S:22]([CH3:25])(=[O:23])=[O:24])[CH:16]=1)#[N:19]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium saltHCID 581337504-Formyl-3-(methylsulfonyl)benzonitrile

Product 1

HCID 86732345tert-Butyl (4-Cyano-2-(methylsulfonyl)phenyl)(phenylsulfonyl)methylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Formic acid (6.2 mL, 164 mmol) is added to a solution of tert-butyl carbamate (3.05 g, 26.0 mmol), 4-formyl-3-(methylsulfonyl)benzonitrile (5.44 g, 26.0 mmol) and sodium benzenesulfinate (4.27 g, 26.0 mmol) in a mixture of tetrahydrofuran (10 mL) and water (25 mL), and the mixture is stirred at room temperature for 4 days. Water (30 mL) is added, and the precipitate is filtered, washed with water and acetonitrile and dried Yield: 5.10 g. ESI mass spectrum: [M+H]+=451; Retention time HPLC: 0.59 min (X012_S01).

Workup

  1. filtrationthe precipitate is filtered
  2. washwashed with water and acetonitrile
  3. customdried Yield: 5.10 g
  4. custom0.59 min (X012_S01)

Sources & evidence

ORD record
ord-32aa409d04774801a98b388e1c852441
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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