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

HRID 59648

Reaction equation

HRID 59648 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+]>C1COCC1.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 mixture of tert-butyl carbamate (3.05 g, 26.0 mmol), 4-formyl-3-(methylsulfonyl)benzonitrile (5.44 g, 26.0 mmol, preparation according to WO09080199) and sodium benzenesulfinate (4.27 g, 26.0 mmol) in THF (10.0 mL) and water (25.0 mL) and the reaction mixture is stirred at room temperature for 4 days. Water (30 mL) is added and the precipitate is filtered off, 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 off
  2. washwashed with water and acetonitrile
  3. customdried
  4. custom0.59 min (X012_S01)

Sources & evidence

ORD record
ord-582eeaa3a7854d5db29ff3a2da6a047e
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Linked notes

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