Benzyl Bromide → Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

HRID 2356130Notes

Reaction equation

HRID 2356130 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.[Ag]=O>[CH2:16]([O:4][CH2:3][C@@H:2]([C:5]([O:7][CH3:8])=[O:6])[NH:1][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 495564Methyl N-(tert-butoxycarbonyl)serinate

Product 1

HCID 14427182Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of BOC-DL-Ser-OMe (434 mg, 2.0 mmol), benzyl bromide (513 mg, 3.0 mmol), and silver oxide (695 mg, 3.0 mmol) in dichloromethane (10 mL) at room temperature was stirred for 2 days, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 308 (M−H)−.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fb8e6fe6a8f846d09bb6f7b2f682aa81
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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