Triethylamine → HCID 70094445, compound

HRID 1075638Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:25](CC)CC)C.ClC(OCC)=O.N[C@@H:37]1[C:43](=[O:44])[N:42]2[C@@H:38]1[O:39][CH2:40][CH2:41]2>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([C@H:37]1[C:43](=[O:44])[N:42]2[C@@H:38]1[O:39][CH2:40][CH:41]2[NH2:25])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -2.5 °C

Procedure

To a solution of N-benzyloxycarbonyl-L-phenylalanine (867 mg, 2.90 mmole) and triethylamine (323 mg, 3.2 mmole) in dichloromethane (20 ml), ethyl chloroformate (315 mg, 2.90 mmole) was added at -15° C. The reaction mixture was stirred at -10 to 5° C. for 1.5 hrs. Then a precooled (~-15° C.) solution of (5R,6S)-6-amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one in ethyl acetate (see above) was added at -15° C. and the resulting mixture was stirred at room temperature for 10 hrs. 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 (55:45) as eluent and 205 mg of the title compound was obtained as white solid.

Workup

stirringthe resulting mixture was stirred at room temperature for 10 hrs
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-d873c7354f284b6aba7483b857444abf
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905076

Reaction notes

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