Boron trifluoride etherate → N-p-Methoxybenzyloxycarbonyl-O-methyl-D-serine benzyl ester

HRID 3777

反応式

HRID 3777 の反応式
[CH2:1]([O:8][C:9](=[O:26])[C@@H:10]([CH2:24][OH:25])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](=O)=O.CC(C)=O.B(F)(F)F.CCOCC.[N+](=C)=[N-]>ClCCl>[CH2:1]([O:8][C:9](=[O:26])[C@@H:10]([CH2:24][O:25][CH3:27])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8000Boron trifluoride etherateHCID 9550DiazomethaneHCID 13652495N-p-methoxybenzyloxycarbonyl-D-serine benzyl esterHCID 18522661Acetone cardice

生成物 1

HCID 13652497N-p-Methoxybenzyloxycarbonyl-O-methyl-D-serine benzyl ester収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester (720 mg, 2.00 mmol) is dissolved in dry dichloromethane (20 ml) and the solution cooled to dry ice/acetone. Boron trifluoride etherate (100 μl) is added followed by the portionwise addition of diazomethane (30 mmol in 20 ml CH2Cl2). After about 30 minutes the solution is filtered and washed once with water (10 ml), then dried (MgSO4) and evaporated to dryness. The resulting residue is chromatographed on silica gel using chloroform as eluant to give the pure title compound as an oil (520 mg, 70%) which crystallises on standing to give a colourless solid of m.p. 68°-69° C.; [α]D20 -1.3° (c 4.0, CHCl3).

後処理

  1. filtrationAfter about 30 minutes the solution is filtered
  2. washwashed once with water (10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe resulting residue is chromatographed on silica gel

出典と根拠

ORDレコード
ord-3d9fe4eea0d14c78998610d953418f18
出典データセット
uspto-grants-1988_02
特許番号
US04722924

関連ノート

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