Triethylamine → Methyl alpha-[4-benzyloxycarbonylthio-3-phthalimido-2-oxoazetidin-1-yl]-alpha-(1-benzyloxycarbonylethylidene)acetate

HRID 325461노트

반응식

HRID 325461 반응식
[SH:1][CH:2]1[N:5]([C:6](=[C:11](O)[CH3:12])[C:7]([O:9][CH3:10])=[O:8])[C:4](=[O:14])[CH:3]1[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].C(N([CH2:42][CH3:43])CC)C>O1CCCC1>[CH2:30]([O:29][C:27]([S:1][CH:2]1[N:5]([C:6](=[C:11]([C:7]([O:9][CH2:10][C:43]2[CH:42]=[CH:23][CH:24]=[CH:17][CH:16]=2)=[O:8])[CH3:12])[C:7]([O:9][CH3:10])=[O:8])[C:4](=[O:14])[CH:3]1[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86735543Methyl alpha-[4-mercapto-3-phthalimido-2-oxoazetidin-1-yl]-alpha-(1-hydroxyethylidene)acetate

생성물 1

HCID 54508360Methyl alpha-[4-benzyloxycarbonylthio-3-phthalimido-2-oxoazetidin-1-yl]-alpha-(1-benzyloxycarbonylethylidene)acetate수율 188.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-65 °C

실험 절차

To a solution of methyl α-[4-mercapto-3-phthalimido-2-oxoazetidin-1-yl]-α-(1-hydroxyethylidene)acetate (100 mg) in tetrahydrofuran (3 ml) is added benzyl chloroformate (100 mg), and the mixture is cooled to -65° C. To the solution is added triethylamine (60 mg) and stirred for 1 hour. After warming to room temperature, the mixture is evaporated. Purification of the residue by chromatography over silica gel gives methyl α-[4-benzyloxycarbonylthio-3-phthalimido-2-oxoazetidin-1-yl]-α-(1-benzyloxycarbonylethylidene)acetate (160 mg). Yield: 94%. The product contains no isomer at position α, IR: νmaxCHCl3 1790, 1780, 1730 cm-1. NMR: δCDCl3 8.00.varies.7.50m4H, 7.40s5H, 7.30s5H, 6.27d(5 Hz)1H, 5.90d(5 Hz)1H, 5.27s2H, 5.17s2H, 3.70s3H, 2.47s3H.

후처리

  1. temperatureAfter warming to room temperature
  2. customthe mixture is evaporated
  3. customPurification of the residue by chromatography over silica gel

출처 및 근거

ORD 기록
ord-75c88a734e6c4d33a55112cc436b9f3a
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440683

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