Ethyl bromoacetate → Boc-L-Trp(CH2COOEt)-OBzl

HRID 1533273Notes

Reaction equation

HRID 1533273 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[OH-].[Na+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(Cl)Cl.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:5]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 10318477Boc-trp-obzl

Product 1

HCID 131722466Boc-L-Trp(CH2COOEt)-OBzlYield 100.1%

Reagents, catalysts & solvents 2

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Boc-L-Trp-OBzl (5.00 g), tetra-n-butylammonium sulfate (43 mg) and NaOH (sodium hydroxide) (1.27 g) in methylene chloride (100 ml) was added a solution of ethyl bromoacetate (5.29 g) in methylene chloride (50 ml) in an ice-bath cooling. After being stirred at room temperature for 2 days, the mixture was washed with 5% aqueous potassium hydrogen sulfate solution, 1M aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo to afford Boc-L-Trp(CH2COOEt)-OBzl (6.10 g) as an oil.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with 5% aqueous potassium hydrogen sulfate solution, 1M aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3c8bd4dedec438c9057137a5b0ff52a
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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