Methyl chloroformate → 3-Alanylamino-1,5-cyclohexadiene carboxylic acid hydrochloride
Reaction equation
C(OC([NH:8][C@H:9]([C:11](O)=[O:12])[CH3:10])=O)(C)(C)C.C(N(CC)CC)C.[Cl:21]C(OC)=O.Cl.[NH2:27][CH:28]1[CH2:33][CH:32]=[CH:31][C:30]([C:34]([O:36]C)=[O:35])=[CH:29]1>ClCCl>[ClH:21].[NH2:8][C@H:9]([C:11]([NH:27][CH:28]1[CH2:33][CH:32]=[CH:31][C:30]([C:34]([OH:36])=[O:35])=[CH:29]1)=[O:12])[CH3:10]Participants
Procedure
A solution of 188 mg (1 m mole) of tert-butoxycarbonylalanine in 5 ml of dichloromethane is treated with 101 mg (1 m mole) of triethylamine and 94 mg (1 m mole) of methyl chloroformate then added to a solution of 190 mg (1 m mole) of methyl 3-amino-1,5-cyclohexadienecarboxylate hydrochloride and 101 mg (1 m mole) of triethylamine in 5 ml of dichloromethane. After 1 hour at 25° C. the solution is washed with water, dried and evaporated. The residue is treated for 3 hours at 25° C. with 3 ml of methanol, 100 mg of sodium hydroxide and 2 ml of water then acidifie and extracted with dichloromethane. The organic phase is dryed and concentrated. The residue is treated with 7 ml of methanol containing 3.5 ml of 5% HCl for 18 hours at 25° C. then concentrated to afford 3-alanylamino-1,5 -cyclohexadiene carboxylic acid hydrochloride.
Workup
- washAfter 1 hour at 25° C. the solution is washed with water
- customdried
- customevaporated
- additionThe residue is treated for 3 hours at 25° C. with 3 ml of methanol, 100 mg of sodium hydroxide and 2 ml of water
- extractionextracted with dichloromethane
- concentrationconcentrated
- additionThe residue is treated with 7 ml of methanol containing 3.5 ml of 5% HCl for 18 hours at 25° C.
- concentrationthen concentrated
Sources & evidence
- ORD record
- ord-d933e6ec7df346daae5f6b63451549bc
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04187316
Reaction notes
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