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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
ノート
印刷プレビュー

反応式

HRID 703583 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒
HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-934663fc26824a969fd5487d4591d234
出典データセット
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04983596

反応ノート

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