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

HRID 2082213

반응식

HRID 2082213 반응식
[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

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetate2회HCID 14798Sodium Hydroxide2회HCID 33992Ethanaminium, N,N,N-trimethyl-, chloride (1:1)HCID 10739405Boc-DTrp-OBzl

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d1aefb68746b414ca25204463bd24e46
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05187156

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