Water → N-benzyloxycarbonyl-l-tyrosine

HRID 1590614Notes

Reaction equation

HRID 1590614 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 712438N-benzyloxycarbonyl-l-tyrosine

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5f7867d2968c48bd8e905017c97e2086
Source dataset
uspto-grants-1993_04
Patent number
US05204350

Reaction notes

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