Water → HCID 59225158, compound

HRID 905644Notes

Reaction equation

HRID 905644 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][N:24]=1)=[O:22])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.O>ClCCl>[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][O:30][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:25][N:24]=1)=[O:22])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59224906HCID 59224906, compound

Product 1

HCID 59225158HCID 59225158, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, methanesulfonyl chloride (4.2 mL, 54 mmol) was added to a solution of N-(2-t-butoxycarbonylaminophenyl)-5-hydroxymethylpyridine-2-carboxylic acid amide (Reference Compound No. 3-1, 16 g, 45 mmol) and triethylamine (16 mL, 110 mmol) in dichloromethane (150 mL), and then the reaction mixture was stirred for 1 hour. Water (400 mL) was added thereto, and then the whole was extracted with ethyl acetate (500 mL) five times. The organic layer was washed with water (500 mL), dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with hexane (80 mL) and ethyl acetate (20 mL) to give 18 g of the title reference compound as a white solid. (Yield 94%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (500 mL) five times
  2. washThe organic layer was washed with water (500 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationThe resulting solid was collected by filtration with hexane (80 mL) and ethyl acetate (20 mL)
  6. customto give 18 g of the title reference compound as a white solid

Sources & evidence

ORD record
ord-6dbb44c7531848b8b8db41e78eb300db
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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