Acetic Acid → benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate

HRID 431758노트

반응식

HRID 431758 반응식
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][N:19]3[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O:57][CH2:58][CH3:59])=O.CC(O)=O>C1COCC1>[C:58]([O:23][C@@H:21]1[CH2:20][N:19]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[C@@H:18]([C:9]2[O:10][C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH2:22]1)(=[O:57])[CH3:59]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86759290benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 86759291benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (1.50 g) and triphenylphosphine (1.43 g) in THF (15 mL) was added diethyl azodicarboxylate (0.86 mL) at 5° C., and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added AcOH (0.29 mL) at 5° C., and the mixture was stirred at room temperature for 3 hours. The reaction mixture was evaporated, and the residue was dissolved in EtOAc, washed with saturated sodium hydrogen carbonate solution, water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 2:1 elution) to give benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate (1.88 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gal column chromatography (hexane-EtOAc, 2:1 elution)

출처 및 근거

ORD 기록
ord-c5037000ad8c408d9a4ad67697f721a2
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660759B1

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