Phenol → (3S,4S)-3-{N-benzyloxycarbonyl-beta-(2-naphthyl)-L-alanyl}-amino-4-phenoxy-azetidin-2-one

HRID 619705Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([O:15][C:16]([NH:18][C@H:19]([C:31]([C@@H:33]1[C@H:36](OC(=O)C)[N:35]([NH2:41])[C:34]1=[O:42])=[O:32])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1COCC1>CC(C)=O.[OH-].[Na+]>[CH2:8]([O:15][C:16]([NH:18][C@H:19]([C:31]([C@@H:33]1[C@H:36]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:35]([NH2:41])[C:34]1=[O:42])=[O:32])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of phenol (30 mg, 0.32 mmol) in acetone (2 ml) and 1 N NaOH (0.25 ml), (3S,4S)-3{N-benzyloxycarbonyl-β-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one (95 mg, 0.2 mmol) in acetone (1 ml) and THF (2 ml) was added at 5° C. The mixture was stirred at 5° C. for 1 hr and then at room temperature for 1 hr. After removal of solvent, the residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:2) as eluent and 45 mg of (3S,4S)-3-{N-benzyloxycarbonyl-β-(2-naphthyl)-L-alanyl}-amino-4-phenoxy-azetidin-2-one was obtained.

Workup

waitat room temperature for 1 hr
customAfter removal of solvent
dissolutionthe residue was dissolved in ethyl acetate
washwashed with water, brine
dry with materialdried over sodium sulfate
customAfter removal of solvent
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-fa131022351b4df78380d10e2d7de6bd
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05959123

Reaction notes

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