Potassium Carbonate → (S)-4-(2-tert-Butoxycarbonylamino-2-methoxycarbonylethyl)-3,5-dimethylbenzoic acid

HRID 1866847노트

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HRID 1866847 반응식
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9](S(C(F)(F)F)(=O)=O)=[CH:8][C:7]=1[CH3:20].[C:30]([O-])([O-:32])=[O:31].[K+].[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:25]([O:24][C:22]([NH:21][C@H:4]([C:3]([O:2][CH3:1])=[O:29])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:30]([OH:32])=[O:31])=[CH:8][C:7]=1[CH3:20])=[O:23])([CH3:28])([CH3:27])[CH3:26]

참가 물질

6

반응물 2

HCID 11430Potassium CarbonateHCID 66893221(S)-2-tert-butoxycarbonylamino-3-(2,6-dimethyl-4-trifluoromethanesulfonylphenyl)-propionic acid methyl ester

생성물 1

HCID 58631279(S)-4-(2-tert-Butoxycarbonylamino-2-methoxycarbonylethyl)-3,5-dimethylbenzoic acid

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a suspension of (S)-2-tert-butoxycarbonylamino-3-(2,6-dimethyl-4-trifluoromethanesulfonylphenyl)-propionic acid methyl ester (9.68 g, 21.3 mmol), K2CO3 (14.1 g, 0.102 mol), Pd(OAc)2 (0.48 g, 2.13 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (2.56 g, 4.47 mmol) in DMF (48 mL) was bubbled in gaseous CO for 15 min. The mixture was heated to 60° C. for 8 h with a CO balloon. The cool mixture was partitioned between NaHCO3 and EtOAc, and filtered. The aqueous layer was separated, acidified with 10% citric acid aqueous solution, extracted with EtOAc, and finally dried over Na2SO4. Filtration and concentration of the filtrate resulted in a residue. The residue was recrystallized from EtOAc-hexanes to yield the desired product.

후처리

  1. customwas bubbled in gaseous CO for 15 min
  2. customThe cool mixture was partitioned between NaHCO3 and EtOAc
  3. filtrationfiltered
  4. customThe aqueous layer was separated
  5. extractionextracted with EtOAc
  6. dry with materialfinally dried over Na2SO4
  7. filtrationFiltration and concentration of the filtrate
  8. customresulted in a residue
  9. customThe residue was recrystallized from EtOAc-hexanes

출처 및 근거

ORD 기록
ord-3edcbadc15e041848a14538fa5536bbb
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629488B2

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