Sulfuric Acid → HCID 25267402, compound

HRID 1516408Notes

Reaction equation

HRID 1516408 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:44])(=[N:29]C(C3CCCN3C(OC(C)(C)C)=O)=O)=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.S(=O)(=O)(O)O>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:44])(=[NH:29])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 86652063HCID 86652063, compound

Product 1

HCID 25267402HCID 25267402, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-methyl-N-(1-tert-butoxycarbonyl-pyrrolidin-2-carbonyl)sulfoximide (1.2 g, 0.00182 mol, nonpolar isomer) in methanol (4 mL) was added conc. sulfuric acid (0.7 g, 0.00728 mol) at 5-10° C. The reaction mixture was stirred at 25-30° C. for 4 hr and then diluted with water. Product obtained was extracted in chloroform at 8-9 pH. Organic layer was dried and concentrated to give 640 mg of titled product in 63% yield.

Workup

  1. customProduct obtained
  2. extractionwas extracted in chloroform at 8-9 pH
  3. customOrganic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-01adc4232ee245aba1dc395fa3eb4224
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

Loading…