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

HRID 217633ノート

反応式

HRID 217633 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67049798HCID 67049798、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-03fb43531c43470f96b1ddf1467c9168
出典データセット
uspto-grants-2012_06
特許番号
US08198271B2

反応ノート

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