Benzyl Alcohol → HCID 14083110, compound
Reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(Cl)(Cl)=O>CCOCC>[CH2:10]([O:8][C:7](=[O:9])[C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[NH2:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
According to the general procedure outlined in J. Med. Chem. 1986, Vol. 30, p. 3575, 15.0 g norleucine (Nle) was mixed with 200 ml benzyl alcohol and cooled to 0° C. Thionyl chloride (25 ml) was added dropwise over 15 minutes and the mixture was slowly heated to 90° C. with a fierce evolution of SO2 occurring at about 50° C. After 2 hours at 90° C. the mixture was cooled to 0° C. and 25 ml more thionyl chloride was added. The mixture was then heated again at 90° C. for 2 hours, cooled, diluted with 1.6 liters ether and stored overnight at 0° C. The crystals which formed were filtered, washed with ether and dried to give 23.1 g of a damp solid which was recrystallized from 1:10 ethanol-ether, using 23 ml ethanol. The filtered and dried solid weighed 17.1 g, TLC Rf 0.25 in System C (the spotted plate was exposed to ammonia vapor and dried prior to elution).
Workup
- temperaturethe mixture was slowly heated to 90° C. with a fierce evolution of SO2 occurring at about 50° C
- temperatureAfter 2 hours at 90° C. the mixture was cooled to 0° C.
- temperatureThe mixture was then heated again at 90° C. for 2 hours
- temperaturecooled
- customThe crystals which formed
- filtrationwere filtered
- washwashed with ether
- customdried
Sources & evidence
- ORD record
- ord-da0ff2a7e7e04df5a5838837d4e4df80
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855303
Reaction notes
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