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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → methyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate

HRID 2392928
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HRID 2392928 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:28])[CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[H][H]>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:28])[CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-2회HCID 24287Tin tetrachlorideHCID 11036381methyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 18980747methyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate수율 87.4%

시약·촉매·용매

1
HCID 887Methanol용매

실험 절차

22.6 g (58.8 mmol) of methyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate, 435 mg (0.39 mmol) of [RuI(p-cymene)(S)-BINAP]I, 72 mg (0.39 mmol) of tin chloride and 364 mg (1.56 mol) of camphor-10-sulfonic acid (hereinafter referred to as "CSA") were placed in a 500 ml autoclave. After air in the autoclave was replaced with nitrogen, 160 ml of methanol was added to the mixture. The nitrogen in the autoclave was replaced with hydrogen and then the mixed solution was reacted at 80° C. under a hydrogen pressure of 80 kg/cm2 for 40 hours. After the completion of the reaction was confirmed by means of HPLC, the reaction solution was concentrated under reduced pressure. The residue was then purified by means of SGIC (eluent: hexane/ethylacetate=2/1 by volume) to prepare the target compound as a colorless oil in an amount of 37.4 g at a yield of 87.4%. The products were analyzed using HPLC. As a result, the rate of the syn-form to the anti-form was 76.3:23.7 and the optical purity of each of the forms was 95.6% ee and 97.8% ee respectively. The analytical results on the target compound are given below.

후처리

  1. additionwas added to the mixture
  2. customthe mixed solution was reacted at 80° C. under a hydrogen pressure of 80 kg/cm2 for 40 hours
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe residue was then purified by means of SGIC (eluent: hexane/ethylacetate=2/1 by volume)
  5. customto prepare the target compound as a colorless oil in an amount of 37.4 g at a yield of 87.4%
  6. customThe analytical results on the target compound

출처 및 근거

ORD 기록
ord-d22d4d91df2d441ab7169068ba1afe76
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05801271

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