Ammonium Chloride → (+/-)-5-Amino-6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl ester hydrochloride
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[C:10](OC)=[N:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl-:26].[NH4+:27]>CO>[ClH:26].[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[C:10]([NH2:27])=[N:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 39.00 g (112.93 mmol) of (+/−)-6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-methoxy-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl ester dissolved in 350 mL of methanol was added 6.34 g (118.57 mmol) of ammonium chloride at room temperature. The resulting mixture was stirred under reflux for 12 h. The cooled solution was evaporated to remove solvent. The residue was triturated with diethyl ether and filtered to afford 33.00 g (80%) of (+/−)-5-Amino-6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl ester hydrochloride (1:1) as a white powder. The compound was used as such in the next step.
Workup
- temperatureunder reflux for 12 h
- customThe cooled solution was evaporated
- customto remove solvent
- customThe residue was triturated with diethyl ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-6e2605d0e0124df390bc66462a30956d
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507476B2
Reaction notes
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