Acetyl chloride → (8R,9aR)-8-[(5-cyclopropylpyrazin-2-yl)oxy]octahydro-5H-pyrrolo[1,2-a][1,4]diazepin-5-one hydrochloride
Reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:28][N:14]4[C:15](=[O:27])[CH2:16][CH2:17][N:18](C(OC(C)(C)C)=O)[CH2:19][C@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C([Cl:32])(=O)C>CO>[ClH:32].[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:28][N:14]4[C:15](=[O:27])[CH2:16][CH2:17][NH:18][CH2:19][C@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
tert-Butyl (8R,9aR)-8-[(5-cyclopropylpyrazin-2-yl)oxy]-5-oxohexahydro-1H-pyrrolo[1,2-a][1,4]diazepine-2(3H)-carboxylate (50 mg, 0.103 mmol, Part A) was dissolved in methanol (1.0 mL) in a 20-mL scintillation vial. In a separate 4-mL vial, acetyl chloride (0.090 ml, 1.29 mmol) was added to methanol (0.5 mL) at 0° C., and the resulting acidic solution was added to the reaction vial. The vial was capped, and the reaction mixture was heated to 60° C. for 0.5 hour. The reaction mixture was then cooled to room temperature and concentrated to provide (8R,9aR)-8-[(5-cyclopropylpyrazin-2-yl)oxy]octahydro-5H-pyrrolo[1,2-a][1,4]diazepin-5-one hydrochloride that was used in the next step without additional purification.
Workup
- additionthe resulting acidic solution was added to the reaction vial
- customThe vial was capped
- temperatureThe reaction mixture was then cooled to room temperature
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4b266efb17c3438d9abd21fd4b0770c3
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382258B2
Reaction notes
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