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

HRID 2082213

反応式

HRID 2082213 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 131717763Boc-D-Trp(CH2CO2Et)-OBzl収率 113.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d1aefb68746b414ca25204463bd24e46
出典データセット
uspto-grants-1993_02
特許番号
US05187156

関連ノート

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