Sodium hydride → HCID 22940770、化合物

HRID 1418787

反応式

HRID 1418787 の反応式
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[H-].[Na+].Br[CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34].C(=O)(O)[O-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:21][CH:22]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 1235321-Bromo-3,6-dioxaheptaneHCID 516892Sodium BicarbonateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

生成物 1

HCID 22940770HCID 22940770、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

6.59 g (20 mmol) of N-benzyloxycarbonyl-tyrosine-methyl ester is dissolved in 25 ml of anhydrous N,N-dimethylformamide and mixed at 0° C. under argon with 0.81 g (20.5 mmol) of sodium hydride dispersion (60% in mineral oil). The batch is allowed to stir for 10 minutes, then 3.75 g (20.5 mmol) of 1-bromo-2-(2-methoxyethoxy)-ethane is added, the reaction temperature is allowed to increase to room temperature and stirred for another three hours. For working-up, the batch is taken up in toluene and shaken out several times against aqueous sodium bicarbonate solution. The organic phase is separated, dried on magnesium sulfate, filtered and concentrated by evaporation. The oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine.

後処理

  1. stirringstirred for another three hours
  2. customThe organic phase is separated
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine

出典と根拠

ORDレコード
ord-1341ac2f27f648288d7130e58f5f5e93
出典データセット
uspto-grants-1999_03
特許番号
US05885548

関連ノート

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