Sulfuric Acid → [(4-Acetyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642377

반응식

HRID 642377 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:11][C:7]=2[C:6]([OH:18])=[C:5]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[N:4]=1)#[CH:2].S(=O)(=O)(O)[OH:27]>CC(C)=O.S([O-])([O-])(=O)=O.[Hg+2]>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:11][C:7]=2[C:6]([OH:18])=[C:5]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[N:4]=1)(=[O:27])[CH3:2]

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 24757507[(4-Ethynyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

생성물 1

HCID 24757508[(4-Acetyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid수율 43.1%

시약·촉매·용매 2

HCID 24544Mercuric sulfate촉매HCID 180Acetone용매

실험 절차

A mixture of [(4-ethynyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid (52 mg, 0.15 mmole), mercury sulfate (44 mg, 0.15 mmole), concentrated sulfuric acid (19 mg, 0.19 mmole) in 80% aqueous acetone (1.6 ml) was refluxed for 2 h before it was cooled to room temperature and concentrated. The residue was washed with water and filtered. The remaining solid was dissolved in 0.5 N NaOH (15 ml) and extracted with dichloromethane (2×20 ml). The remaining aqueous layer was acidified with 1N HCl (8 ml) to pH=2. The suspension was extracted with ethyl acetate (20 ml) and dichloromethane (20 ml). The organic layer was combined, concentrated and purified by column chromatography on a C18 column with a gradient of water and acetonitrile in formic acid to give the title compound as a yellow solid (24 mg): MS: (+) m/z 372.24 (M+1), MS: (−) m/z 370.27 (M−1).

후처리

  1. temperaturewas refluxed for 2 h before it
  2. concentrationconcentrated
  3. washThe residue was washed with water
  4. filtrationfiltered
  5. dissolutionThe remaining solid was dissolved in 0.5 N NaOH (15 ml)
  6. extractionextracted with dichloromethane (2×20 ml)
  7. extractionThe suspension was extracted with ethyl acetate (20 ml) and dichloromethane (20 ml)
  8. concentrationconcentrated
  9. custompurified by column chromatography on a C18 column with a gradient of water and acetonitrile in formic acid

출처 및 근거

ORD 기록
ord-fcff9ae8bd1447399e97f86b7eff9179
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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