Hydrochloric Acid → Boc-D-Trp(CH2CO2Et)-OBzl

HRID 2082213

Reaction equation

HRID 2082213 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+].[Cl-].C([N+](C)(C)C)C.Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].Cl>C(Cl)Cl>[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]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetate2×HCID 14798Sodium Hydroxide2×HCID 33992Ethanaminium, N,N,N-trimethyl-, chloride (1:1)HCID 10739405Boc-DTrp-OBzl

Product 1

HCID 131717763Boc-D-Trp(CH2CO2Et)-OBzlYield 113.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-D-Trp-OBzl (3.0 g) in methylene chloride (60 ml) were added powdered sodium hydroxide (1.52 g), ethyltrimethylammonium chloride (150 mg) and ethyl bromoacetate (2.54 g). The mixture was stirred overnight at room temperature, then powdered sodium hydroxide (0.61 g) and ethyl bromoacetate (0.63 g) were added. The mixture was stirred further for four and half an hour at room temperature and for two hours under reflux. After cooling, 1N-hydrochloric acid (53 ml) was added to the mixture, and the organic layer was washed with sodium chloride solution and dried with magnesium sulfate. After evaporation, the residue (4.87 g) was chromatographed on a silica gel column (60 g) eluting successively with chloroform and chloroform-ethyl acetate (4:1) to give a purified Boc-D-Trp(CH2CO2Et)-OBzl (4.14 g).

Workup

  1. stirringThe mixture was stirred further for four and half an hour at room temperature and for two hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. washthe organic layer was washed with sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. customAfter evaporation
  7. customthe residue (4.87 g) was chromatographed on a silica gel column (60 g)
  8. washeluting successively with chloroform and chloroform-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-d1aefb68746b414ca25204463bd24e46
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Linked notes

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