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

HRID 325461Notes

Reaction equation

[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

Participants

Conditions

Temperature: -65 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-75c88a734e6c4d33a55112cc436b9f3a
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04440683

Reaction notes

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