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Methyl 3-oxovalerate → 2-[(4-{2-[Heptyl(3-oxopentanoyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914377
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HRID 914377 반응식
[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:27][CH2:28][C:29]([CH2:31][C:32](OC)=[O:33])=[O:30]>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:32](=[O:33])[CH2:31][C:29](=[O:30])[CH2:28][CH3:27])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]
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4

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HCID 121699Methyl 3-oxovalerateHCID 597593122-({4-[2-(Heptylamino)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester

생성물 1

HCID 873855042-[(4-{2-[Heptyl(3-oxopentanoyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester수율 42.8%

시약·촉매·용매 1

HCID 7237O-Xylene용매

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온도
135 °C

실험 절차

2-({4-[2-(Heptylamino)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester (3.0 g) synthesized in Example 303-2 and 3-keto-n-valeric acid methyl ester (1.46 g) were dissolved in xylene (10 mL), and the mixture was stirred at 135° C. for 8 hr. After cooling to room temperature, the solution was directly packed and purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give 2-[(4-{2-[heptyl(3-oxopentanoyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (1.6 g) as a colorless oil. The present compound was used in the next step without particular purification. The title compound was obtained by an operation similar to that of Example 446 for the steps after cyclization reaction using hydrazine monohydrate.

후처리

  1. temperatureAfter cooling to room temperature
  2. custompurified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-b008a288b2a44333b2dc38af9db85b60
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08026370B2

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