Hydrochloric Acid → HCID 86758038, compound
Reaction equation
C([O:3][C:4](=[O:33])[C@@H:5]([NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:6][NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:25])/[CH:17]=[CH:18]/[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:11]1)=[O:9])C.Cl.C(OCC)(=[O:37])C>>[F:29][C:28]([F:31])([F:30])[C:27]([OH:32])=[O:37].[NH:22]1[CH2:23][CH2:24][CH:19](/[CH:18]=[CH:17]/[C:16]([N:12]2[CH2:13][CH2:14][CH2:15][C@@H:10]([C:8]([NH:7][CH2:6][C@H:5]([NH:26][C:27](=[O:32])[C:28]([F:29])([F:30])[F:31])[C:4]([OH:33])=[O:3])=[O:9])[CH2:11]2)=[O:25])[CH2:20][CH2:21]1Participants
Procedure
To a stirred solution of N-[(R)-1-[3-(4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-2(S)-trifluoroacetylamino-β-alanine ethyl ester (334 mg, 0.58 mmol) in ethyl acetate (1.5 ml) was added a solution of 4N-hydrogen chloride in ethyl acetate (1.0 ml, 4 mmol). After the solution was stirred for 2 hours at ambient temperature, the solvent was evaporated in vacuo. The residue was dissolved in 0.1M phosphate buffer (pH=7.3, 200 ml). To the solution was added Porcine liver esterase (0.5 ml), and the solution was stirred for 7 days at ambient temperature. Solvent was evaporated, and the residue was purified by HPLC to give N-[(R)-1-[3-(4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-2(S)-trifluoroacetylamino-β-alanine trifluoroacetate as a colorless oil (220 mg, 67.5%).
Workup
- customthe solvent was evaporated in vacuo
- dissolutionThe residue was dissolved in 0.1M phosphate buffer (pH=7.3, 200 ml)
- additionTo the solution was added Porcine liver esterase (0.5 ml)
- stirringthe solution was stirred for 7 days at ambient temperature
- customSolvent was evaporated
- customthe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-2664167e39544728893d89e9d73b7d43
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384028B1
Reaction notes
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