Lithium borohydride → 5-(2-Hydroxyethyl)-N-{[6-(hydroxymethyl)-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}-4-methylthiophene-2-sulfonamide

HRID 1696776노트

반응식

HRID 1696776 반응식
C([O:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([S:12]([NH:15][C:16]([NH:18][C:19]2[N:24]=[C:23]([C:25](OC)=[O:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)=[O:17])(=[O:14])=[O:13])=[CH:9][C:8]=1[CH3:33])(=O)C.[BH4-].[Li+]>O1CCCC1>[OH:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([S:12]([NH:15][C:16](=[O:17])[NH:18][C:19]2[CH:20]=[C:21]([C:29]([F:31])([F:32])[F:30])[CH:22]=[C:23]([CH2:25][OH:26])[N:24]=2)(=[O:14])=[O:13])=[CH:9][C:8]=1[CH3:33]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 42630611Methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate

생성물 1

HCID 672743805-(2-Hydroxyethyl)-N-{[6-(hydroxymethyl)-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}-4-methylthiophene-2-sulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.100 g methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate in 1.5 ml tetrahydrofuran was added 0.02 g lithiumborohydride and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated. The organic phase was washed with water. To he combined water phases was added 1 ml 10% citric acid and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and evaporated to yield the title compound as white foam (containing acetoxy and hydroxyethyl ca 1:1) The mixture was dissolved in ca 2 ml methanol and ca 0.05 ml 28% sodium hydroxide and kept at room temperature for 5 h. The reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine and evaporated to yield 0.049 g of the title compound as white foam. MS (ISN) M−H+=438.4

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe phases were separated
  3. washThe organic phase was washed with water
  4. additionwas added 1 ml 10% citric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. customevaporated

출처 및 근거

ORD 기록
ord-7d52fae8c2a04dddb7d5dffcb121197a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163778B2

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