Glycine → {[7-Hydroxy-3-(4-methoxy-phenyl)-4-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 2388219노트

반응식

HRID 2388219 반응식
[OH:1][C:2]1[C:3]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C:4]=2[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:30][CH2:31][C:32]([OH:34])=[O:33].C[O-].[Na+]>C(=O)(O)[O-].[Na+]>[OH:1][C:2]1[C:3]2[O:21][N:20]=[C:19]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:4]=2[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:6][C:7]=1[C:8]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:9]

참가 물질

5

반응물 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67531952Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

생성물 1

HCID 42633243{[7-Hydroxy-3-(4-methoxy-phenyl)-4-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid수율 62.3%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (70 mg, 0.18 mmol) and glycine (539 mg, 7.18 mmol) were added to sodium methoxide solution (10.8 mL, 5.38 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in minimum amount of water and 0.25 M hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 79 mg of crude solid. The solid was dissolved in 15 mL of saturated sodium bicarbonate solution and washed with hexanes and EtOAc. The aqueous layer was acidified to pH 3 with concentrated hydrochloric acid and the precipitate was collected by filtration. The solid was dried under vacuum to afford 47 mg of the title compound. MS: (+) m/z 420.37 (M+1).

후처리

  1. temperaturethe mixture was refluxed for 3 days
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in minimum amount of water and 0.25 M hydrochloric acid
  4. additionwas added until pH was 3
  5. customThe precipitate was isolated by filtration
  6. customdried under vacuum
  7. customto give 79 mg of crude solid
  8. washwashed with hexanes and EtOAc
  9. filtrationthe precipitate was collected by filtration
  10. customThe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-06a55c5459114adf9747edcf121160c7
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269008B2

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