Dichloromethane → HCID 18664242, compound
Reaction equation
[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][C@@H:3]([C:11]([OH:13])=[O:12])[NH:2]1.C(=O)([O-])O.[Na+].ClCCl.[C:22](OC(=O)C)(=[O:24])[CH3:23]>O>[C:22]([N:2]1[C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C@@H:5]2[C@@H:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:1]1)(=[O:24])[CH3:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture comprising (4aR,8aS) isomer, (4aR,8aR) isomer and trans isomer of decahydroisoquinoline-3(S)-carboxylic acid was dissolved in 72 ml of water, followed by the addition of 60.9 g (725 mmol) of sodium hydrogencarbonate and 72 ml of dichloromethane at room temperature. Thereafter, 27.4 ml (290 mmol) of acetic anhydride was slowly dropwise added thereto, followed by stirring for 22 hours. Insolubles were separated by filtration. After 6N hydrochloric acid was poured thereinto to adjust to pH3, common salt was added thereto up to saturation. Extraction with chloroform was conducted and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure. Dichloromethane was added thereto to thereby obtain 5.45 g of a crystal of the title compound. Yield 33.4% (two steps).
Workup
- customInsolubles were separated by filtration
- additionAfter 6N hydrochloric acid was poured
- additionwas added
- extractionExtraction with chloroform
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated in a reduced pressure
- additionDichloromethane was added
Sources & evidence
- ORD record
- ord-683316f2e10644bbb37ae1b881bebb56
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789403
Reaction notes
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