Triethylamine → HCID 86754247, compound
Reaction equation
[O:1]=[C:2]1[N:8]2[CH:4]([O:5][CH:6]([CH2:9][C:10]([O-:12])=O)[CH2:7]2)[CH2:3]1.[Na+].ClC(OCC)=O.Cl.[CH2:21]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CS(C)=O.ClCCl.C(Cl)(Cl)Cl>[CH2:21]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:10]([CH2:9][CH:6]1[O:5][CH:4]2[N:8]([C:2](=[O:1])[CH2:3]2)[CH2:7]1)=[O:12])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -15 °C
Procedure
To solution of sodium 2-(7-oxo-4-oxa-1-azabicyclo [3,2,0] heptan-3-yl)-acetate (194 mg, 1 mmol) in 2 ml of DMSO and 10 ml of dichloromethane, ethyl chloroformate (109 mg, 1 mmol) was added at -15° C. After stirring at -15° C. for 30 mins, a precooled (ca. -10° C.) solution of L-proline benzyl ester hydrochloride (242 mg, 1 mmol), triethylamine (110 mg, 1.1 mmol) in chloroform (8 ml) was added at -10° C. The resulting mixture was stirred at -10 to 0° C. for 2 hrs and at room temperature overnight, and then diluted with chloroform, washed with water, dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:2) as eluent and 80 mg of the title compound was obtained.
Workup
- stirringThe resulting mixture was stirred at -10 to 0° C. for 2 hrs and at room temperature overnight
- washwashed with water
- dry with materialdried over sodium sulfate
- customAfter removal of solvent
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-aa034d6665ef45d08c50f362d4641444
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05925633
Reaction notes
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