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tert-Butyl mercaptan → (5-{4-tert-Butylsulfanyl-2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid

HRID 554639
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인쇄 미리보기

반응식

HRID 554639 반응식
[H-].[Na+].[CH3:3][C:4]([SH:7])([CH3:6])[CH3:5].C([O:10][C:11](=[O:35])[CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22](F)=[CH:21][C:20]=2[CH2:26][N:27]([C:30]([CH:32]2[CH2:34][CH2:33]2)=[O:31])[CH2:28][CH3:29])[CH:18]=1)C>CN(C=O)C.O.N#N>[C:4]([S:7][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[CH:18]=[C:13]([CH2:12][C:11]([OH:35])=[O:10])[CH:14]=[N:15][CH:16]=2)=[C:20]([CH2:26][N:27]([C:30]([CH:32]2[CH2:34][CH2:33]2)=[O:31])[CH2:28][CH3:29])[CH:21]=1)([CH3:6])([CH3:5])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 58565012(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

생성물 1

HCID 45138778(5-{4-tert-Butylsulfanyl-2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid

시약·촉매·용매 3

HCID 947Nitrogen
용매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (60% in mineral oil; 0.042 g, 1.04 mmol) was suspended in DMF (5 mL). After stirring for 10 minutes, 2-methyl-2-propanethiol (0.13 mL, 1.15 mmol) was added, and the mixture was stirred for 30 minutes. (5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.20 g, 0.52 mmol) was added, and the reaction was stirred at 90° C. overnight. The mixture was diluted with H2O, and N2 was bubbled through the solution into a bleach trap until all odor was removed. The aqueous layer was washed with EtOAc, and then acidified to pH 4 and extracted with EtOAc. The combined organic layers were concentrated, and the residue was purified by preparative HPLC to give Compound 22.

후처리

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringthe reaction was stirred at 90° C. overnight
  3. customwas bubbled through the solution into a bleach trap until all odor
  4. customwas removed
  5. washThe aqueous layer was washed with EtOAc
  6. extractionextracted with EtOAc
  7. concentrationThe combined organic layers were concentrated
  8. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-d857485f4ea04e04a8c56b161bd5d003
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08049015B2

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