Water → HCID 57073292, compound

HRID 619708Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@H:24]([O:25][C:26](=O)[CH3:27])[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1COCC1>[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@H:24]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@@H:24]([O:25][C:26]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:27]=2)[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of phenol (2.82 g 30 mmole) in THF (30 ml) and 1N NaOH (26 ml, 26 mmole), (3S, 4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one (5.56 g, 20 mmole) in THF (40 ml) and H2O (20 ml) is added at 0° C. The mixture is stirred at 0° C for 1 hour and then at room temperature for 30 min. After removal of solvent, the residue is dissolved in ethyl acetate, washed with water, brine and dried over sodium sulphate. After removal of solvent, the residue is purified by silica gel column chromatography using hexane-ethyl acetate as eluent. 2.75 g of (3S, 4S)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (A), 890 mg of (3S, 4R)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (B) and 1.08 g of a mixture of (A) and (B) is obtained.

Workup

waitat room temperature for 30 min
customAfter removal of solvent
dissolutionthe residue is dissolved in ethyl acetate
washwashed with water, brine
dry with materialdried over sodium sulphate
customAfter removal of solvent
customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-7d2a6508254449269e856a6bf57e5bdb
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05959123

Reaction notes

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