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7-Hydroxy-4-(2-methyl-allyl)-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester → 7-Hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642339
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HRID 642339 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][C:13]([CH3:15])=[CH2:14])[C:9]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:18][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2]>C(OCC)(=O)C.C(O)C.C(O)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]2[N:16]=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[S:18][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 1

HCID 684283547-Hydroxy-4-(2-methyl-allyl)-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 684281637-Hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester수율 27.3%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 284Formic Acid용매HCID 702Ethanol용매
HCID 8857
Ethyl Acetate
용매

실험 절차

A mixture of 7-hydroxy-4-(2-methyl-allyl)-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (128 mg, 0.36 mmole) and 10% Pd/C (100 mg) in ethyl acetate (12 ml), ethanol (3 ml) and formic acid (15 μl) was hydrogenated at 20 psi for a week before it was filtered, concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The sodium bicarbonate layer was washed with dichloromethane. The organic layer was combined and washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (35 mg). MS: (+) m/z 356.96 (M+1).

후처리

  1. waitwas hydrogenated at 20 psi for a week before it
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe sodium bicarbonate layer was washed with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-60a124e66db54f73bda029e8512c57f8
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696223B2

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