Sodium Hydroxide → Boc-D-Trp(Tos)-OH

HRID 2082212Notes

Reaction equation

HRID 2082212 reaction equation
[NH:1]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@@H:2]([C:23]([O:25]CC1C=CC=CC=1)=[O:24])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:5]=1.[OH-].[Na+]>C(O)C>[NH:1]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@@H:2]([C:23]([OH:25])=[O:24])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 131717761Boc-D-Trp(Tos)-OBzl

Product 1

HCID 131717762Boc-D-Trp(Tos)-OHYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice cooled solution of Boc-D-Trp(Tos)-OBzl (3.23 g) in ethanol (40 ml) was added 1N sodium hydroxide solution (6 ml) at room temperature. The solution was stirred for two hours, during this period two 2 ml portions of 1N sodium hydroxide solution were added. After evaporation of ethanol, and addition of water (50 ml), the solution was extracted once with ether. The aqueous layer was acidified with 1N hydrochloric acid and the resulting oily material was extracted with ethyl acetate, and the extract was washed with sodium chloride, and dried over magnesium sulfate. Evaporation gave Boc-D-Trp(Tos)-OH (2.5 g) as an amorphous solid.

Workup

  1. additionwere added
  2. customAfter evaporation of ethanol, and addition of water (50 ml)
  3. extractionthe solution was extracted once with ether
  4. extractionthe resulting oily material was extracted with ethyl acetate
  5. washthe extract was washed with sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation

Sources & evidence

ORD record
ord-85f48b169c044e2d9dfffd934b953fea
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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