Allyl bromide → N-(t-Butoxycarbonyl)-D-tryptophan Allyl Ester

HRID 1918

Reaction equation

HRID 1918 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[CH:30]=[CH2:31]>CC(C)=O>[CH2:31]([O:21][C:20](=[O:22])[C@@H:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:30]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophan

Product 1

HCID 53861219N-(t-Butoxycarbonyl)-D-tryptophan Allyl EsterYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(t-Butoxycarbonyl)-D-tryptophan (3 g; 9.868 mmol) was dissolved in acetone and an aqueous solution of potassium carbonate (2.84 g; 20.58 mmol) added followed by allyl bromide (1.55 g; 12.81 mmol). The reaction mixture was stirred for 18 h and then the acetone was substantially removed by evaporation under reduced pressure. The oily water layer that remained was acidified to approximately pH=5 with 1N-hydrochloric acid and then extracted with methylene chloride. The methylene chloride layer was dried over anhydrous magnesium sulfate powder, filtered and evaporated under reduced pressure to give a foamy solid. The foam was further purified by column chromatography using silica gel and ethyl acetate and hexanes 2:1 v/v as eluant. In this manner, a 1.92 g yield (56%) of the desired product was obtained as an off white solid. FAB-MS:- calculated for C19H24N2O4 344; found 344 (M).

Workup

  1. customthe acetone was substantially removed by evaporation under reduced pressure
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate powder
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a foamy solid
  7. customThe foam was further purified by column chromatography

Sources & evidence

ORD record
ord-76eb407e00c64615a297c82a5b981a5c
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Linked notes

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