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

HRID 2063323노트

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HRID 2063323 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-bc62ee5d7f014d85b9bd0a38d30238a0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288380B2

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