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

HRID 982494

반응식

HRID 982494 반응식
[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.B(F)(F)F.[CH3:31]COCC.[N+](=C)=[N-]>ClCCl.C(=O)=O.CC(C)=O>[CH2:1]([O:8][C:9](=[O:26])[C@@H:10]([CH2:24][O:25][CH3:31])[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

참가 물질

6

반응물 3

HCID 8000Boron trifluoride etherateHCID 9550DiazomethaneHCID 13652495N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 18522661Acetone cardice용매

실험 절차

The N-p-methoxybenzyloxycarbonyl-D-serine benzyl ester (720 mg, 2.00 mmol) is dissolved in dry dichloromethane (20 ml) and the solution cooled in 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).

후처리

  1. filtrationis 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

출처 및 근거

ORD 기록
ord-7d05f0a890b44fe78c85110c14523f5e
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04996313

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