Water → N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amide

HRID 217633Notes

Reaction equation

HRID 217633 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][N:23]=2)=[O:21])=[CH:16][S:17][CH:18]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.O>ClCCl.C(OCC)(=O)C>[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][O:29][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:24][N:23]=2)=[O:21])=[CH:16][S:17][CH:18]=1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67049798HCID 67049798, compound

Product 1

HCID 86652250N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amideYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, methanesulfonyl chloride (71 μL, 0.92 mmol) was added to a solution of N-(4-t-butoxycarbonylaminothiophen-3-yl)-5-hydroxymethylpyridine-2-carboxylic acid amide (Reference Compound No. 3-1, 0.32 g, 0.93 mmol) and triethylamine (0.32 mL, 2.3 mmol) in anhydrous dichloromethane (20 mL), and then the reaction mixture was stirred for 2 hour. Water (0.15 L) and ethyl acetate (0.15 L) were added thereto and the whole was partitioned. The organic layer was washed with brine (0.15 L), dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to give 0.36 g of the title reference compound as a yellow solid. (Yield 91%)

Workup

  1. customthe whole was partitioned
  2. washThe organic layer was washed with brine (0.15 L)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customto give 0.36 g of the title reference compound as a yellow solid

Sources & evidence

ORD record
ord-03fb43531c43470f96b1ddf1467c9168
Source dataset
uspto-grants-2012_06
Patent number
US08198271B2

Reaction notes

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