Ammonium formate → Methyl 3-hydroxy-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]benzoate

HRID 548759노트

반응식

HRID 548759 반응식
Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([O:26]CC2C=CC=CC=2)[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20].C([O-])=O.[NH4+]>CO.[Pd]>[OH:26][C:24]1[CH:23]=[C:18]([CH:17]=[C:16]([O:15][C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:14])[N:8]([CH3:13])[CH2:9][CH2:10][O:11][C:12]=3[CH:2]=2)[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 57663169Methyl 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(phenylmethyl)oxy]benzoate

생성물 1

HCID 57663229Methyl 3-hydroxy-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]benzoate수율 50.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of methyl 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(phenylmethyl)oxy]benzoate (8.8 g, 18.8 mmol), and ammonium formate (11.87 g, 188 mmol) in methanol (190 mL) was placed under an atmosphere of argon and 10% palladium on charcoal (880 mg) added. The mixture was heated under relux for 2 hours, cooled to RT, filtered through Celite®, washed with methanol, and the filtrates evaporated in vacuo to a residue which was partitioned between water (150 mL) and ethyl acetate (200 mL). The organic layer was washed with brine, dried (MgSO4), evaporated in vacuo to a residue which was chromatographed on basic alumina, eluting with ethyl acetate then methanol, to give a solid which was crystallised from ethyl acetate and isohexane to give the desired compound (3.25 g). 1H NMR δ (CDCl3): 3.15 (s, 3H), 3.5 (t, 2H), 4.35 (t, 2H), 6.6 (dd, 1H), 6.75 (dt, 1H), 7.8 (t, 1H); m/z 344 (M+H)+

후처리

  1. temperatureThe mixture was heated under relux for 2 hours
  2. filtrationfiltered through Celite®
  3. washwashed with methanol
  4. customthe filtrates evaporated in vacuo to a residue which
  5. customwas partitioned between water (150 mL) and ethyl acetate (200 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo to a residue which
  9. customwas chromatographed on basic alumina
  10. washeluting with ethyl acetate
  11. custommethanol, to give a solid which
  12. customwas crystallised from ethyl acetate and isohexane

출처 및 근거

ORD 기록
ord-b1ee1e035d574a97bb332a0f4ea03e66
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943607B2

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