Benzyl Bromide → HCID 44223288, compound

HRID 722799

Reaction equation

HRID 722799 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][CH3:5].[CH:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:15]([N:1]([C@@H:2]([CH2:3][CH2:4][CH3:5])[C:6]([O:8][CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)=[O:7])[CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)[C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 65098L-Norvaline

Product 1

HCID 44223288HCID 44223288, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of L-norvaline (685 mg, 5.85 mmol) in MeCN (15 mL), BnBr (3.48 mL, 29.24 mmol) and K2CO3 (4.04 g, 29.24 mmol) were added. The mixture was stirred at 60° C. for 9 h, and then cooled down to room temperature and filtered, washing the solid with EtOAc. The filtrates were concentrated in vacuo and the residue purified by column chromatography on silica (100% hexane to hexane/EtOAc 5:1) to obtain benzyl ester 9 as a colorless oil (1.6 g, 71% yield).

Workup

  1. temperaturecooled down to room temperature
  2. filtrationfiltered
  3. washwashing the solid with EtOAc
  4. concentrationThe filtrates were concentrated in vacuo
  5. customthe residue purified by column chromatography on silica (100% hexane to hexane/EtOAc 5:1)

Sources & evidence

ORD record
ord-eaeff5e461914e19836b8db465d0611d
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Linked notes

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