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

HRID 1866847ノート

反応式

HRID 1866847 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3edcbadc15e041848a14538fa5536bbb
出典データセット
uspto-grants-2009_12
特許番号
US07629488B2

反応ノート

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