Morpholine → Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 371282Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:7][C:8]([F:41])([F:40])[CH:9]([CH:11]1[C:17](=[O:18])[N:16]2[CH:12]1[CH2:13][C:14](OS(C1C(C)=CC=CC=1)(=O)=O)=[C:15]2[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[OH:10].C(OC(=O)C)C>CN(C=O)C>[F:41][C:8]([F:7])([F:40])[CH:9]([CH:11]1[C:17](=[O:18])[N:16]2[CH:12]1[CH2:13][C:14]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[C:15]2[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[OH:10]

Participants

Conditions

Temperature: 25 °C

Procedure

Morpholine (17.5 μl) is added to an ice-cold, stirring solution of benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (51 mg) in anhydrous DMF (0.5 ml). The resulting solution is allowed to warm to room temperature (25° C.) and then stirred at room temperature for 4 hrs. Ethylacetate (10 ml) is added and the solution is washed with water (5×2 ml), pH 3 phosphate buffer, 5% NaHCO3, brine, dried with MgSO4, and filtered. Evaporation of the solvent in vacuo leaves benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

washthe solution is washed with water (5×2 ml), pH 3 phosphate buffer, 5% NaHCO3, brine
dry with materialdried with MgSO4
filtrationfiltered
customEvaporation of the solvent in vacuo

Sources & evidence

ORD record: ord-4ef56db0871347bca02087667ed49488
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04530841

Reaction notes

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