Sodium Chloride → O-Benzyl-N-benzyloxycarbonyltyrosinol

HRID 5725

Reaction equation

HRID 5725 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[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].[Cl-].[Li+].[BH4-].[Na+].[Cl-].[Na+]>C(O)C.O1CCCC1>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C@@H:4]([CH2:3][OH:2])[NH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:18][CH:19]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 10916769O-benzyl-N-benzyloxycarbonyltyrosine methyl ester

Product 1

HCID 22863341O-Benzyl-N-benzyloxycarbonyltyrosinolYield 99.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

27.25 g of O-benzyl-N-benzyloxycarbonyltyrosine methyl ester was dissolved in a mixed solvent of 185 ml of ethanol and 122 ml of tetrahydrofuran, and to the solution were added 5.8 g of lithium chloride and 5.2 g of sodium borohydride under ice cooling. The reaction mixture was stirred at a room temperature for 18 hours, and after the addition of 500 ml of saturated sodium chloride aqueous solution, extracted twice with 300 ml of chloroform. The extract was dried over magnesium sulfate and concentrated under a reduced pressure to obtain 25.4 g of the title compound as colorless crystals

Workup

  1. extractionextracted twice with 300 ml of chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-915998a24bba4f2190531cc7ca53e3a6
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Linked notes

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