Water → N-benzyloxycarbonyl-l-tyrosine

HRID 1590614ノート

反応式

HRID 1590614 の反応式
[OH2:1].[H-].[Na+].[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)([O:6][C:7]([CH3:10])(C)C)=[O:5]>CCOC(C)=O.C(Cl)Cl>[C:4]([NH:11][C@H:12]([C:4]([OH:6])=[O:5])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:1])=[CH:18][CH:19]=1)([O:6][CH2:7][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5]

参加物

5

反応物 3

HCID 962WaterHCID 24758Sodium hydrideHCID 103578931,1-Dimethylethyl N-(8-bromooctyl)carbamate

生成物 1

HCID 712438N-benzyloxycarbonyl-l-tyrosine

試薬・触媒・溶媒 1

HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

H2O (1.5 g, 4.29 mmole) was dissolved in EtOAc/CH2Cl2, dried over MgSO4, filtered and evaporated. The residue was dissolved in DMF and treated with NaH (50% dispersion in oil, 0.43 g, 8.96 mmole) for 1 hour. N-BOC-8-amino-1-bromooctane (1.33 g, 4.34 mmole) was added and the reaction was stirred for 16 hours. The DMF was removed in vacuo, the residue dissolved in water, acidified to pH 3 and extracted with EtOAc. The EtOAc layers were combined, dried and concentrated. Column chromatography (SiO2, 97:3:1 CHCl3 /MeOH/HOAc) gave 2-5.

後処理

  1. dry with materialdried over MgSO4
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in DMF
  5. customThe DMF was removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. extractionextracted with EtOAc
  8. customdried
  9. concentrationconcentrated
  10. customColumn chromatography (SiO2, 97:3:1 CHCl3 /MeOH/HOAc) gave 2-5

出典と根拠

ORDレコード
ord-5f7867d2968c48bd8e905017c97e2086
出典データセット
uspto-grants-1993_04
特許番号
US05204350

反応ノート

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