Water → N-benzyloxycarbonyl-l-tyrosine

HRID 1590614노트

반응식

HRID 1590614 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 712438N-benzyloxycarbonyl-l-tyrosine

시약·촉매·용매 1

HCID 21226138Dichloromethane ethylacetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f7867d2968c48bd8e905017c97e2086
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204350

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