Benzyl Alcohol → HCID 14083110, compound

HRID 1087310Notes

Reaction equation

HRID 1087310 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]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 21236CaprineHCID 24386Thionyl Chloride2×

Product 1

HCID 14083110HCID 14083110, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 min. and the mixture was slowly heated to 90° C. with a fierce evolution of SO2 occurring at about 50° C. After 2 h 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 h, cooled, diluted with 1.6 L 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

  1. temperaturethe mixture was slowly heated to 90° C. with a fierce evolution of SO2 occurring at about 50° C
  2. temperatureAfter 2 h at 90° C. the mixture was cooled to 0° C.
  3. temperatureThe mixture was then heated again at 90° C. for 2 h
  4. temperaturecooled
  5. customThe crystals which formed
  6. filtrationwere filtered
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-6b4a031089d54014911b8ebfa5b7e620
Source dataset
uspto-grants-1991_07
Patent number
US05034376

Reaction notes

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