Sodium hydride → Tert-butyl 4-[(2-amino-1,1-dimethylethyl)thio]benzoate

HRID 131297노트

반응식

HRID 131297 반응식
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([SH:6])[CH3:5].[H-].[Na+].F[C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][CH:12]=1>CN(C)C=O.O>[NH2:2][CH2:3][C:4]([S:6][C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:13][CH:12]=1)([CH3:7])[CH3:5]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 2736444Tert-butyl 4-fluorobenzoateHCID 130491041-Amino-2-methyl-2-propanethiol hydrochloride

생성물 1

HCID 69301223Tert-butyl 4-[(2-amino-1,1-dimethylethyl)thio]benzoate수율 75.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 1-amino-2-methyl-2-propanethiol hydrochloride (75 mg) in N,N-dimethylformamide (2 mL) is added sodium hydride (60% dispersion in mineral oil, 50 mg) and the mixture is stirred at room temperature for 30 minutes. To the mixture is added tert-butyl 4-fluorobenzoate (50 mg) and the mixture is stirred at 70° C. for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is concentrated in vacuo and the resultant product is purified by flash column chromatography on NH-silica gel (solvent; ethyl acetate) to give tert-butyl 4-[(2-amino-1,1-dimethylethyl)thio]benzoate (54 mg, yield; 75%) as a colorless oil. MS (APCI) m/z: 282 [M+H]+

후처리

  1. stirringthe mixture is stirred at 70° C. for 4 hours
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract is concentrated in vacuo
  4. customthe resultant product is purified by flash column chromatography on NH-silica gel (solvent; ethyl acetate)

출처 및 근거

ORD 기록
ord-a4326f640f3a4f4ca506856327a301d3
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384952B2

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