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1,8-Diazabicyclo(5.4.0)undec-7-ene → (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

HRID 703583
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인쇄 미리보기

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HRID 703583 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24](OS(C)(=O)=O)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OCC)(=O)C.O.Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

7

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57247090(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

생성물 1

HCID 57248036(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine수율 89.5%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매
HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (3.7 g) in tetrahydrofuran (40 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.1 ml) at ambient temperature and the mixture was stirred for one hour. Removal of the solvent in vacuo gave an oil which was dissolved in a mixture of ethyl acetate (100 ml), water (50 ml) and 1N-hydrochloric acid (10 ml). The organic layer was separated, washed twice with brine (50 ml) and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (2.72 g).

후처리

  1. customRemoval of the solvent in vacuo
  2. customgave an oil which
  3. customThe organic layer was separated
  4. washwashed twice with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on silica gel (200 ml)
  9. washeluting with a mixture of hexane and ethyl acetate (1:1 V/V)

출처 및 근거

ORD 기록
ord-934663fc26824a969fd5487d4591d234
출처 데이터셋
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04983596

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