Sodium Bicarbonate → Ethyl N-(tert-butoxycarbonyl)-L-tyrosinate

HRID 253735

Reaction equation

HRID 253735 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:16])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[C:17]([O-:20])(O)=[O:18].[Na+]>C(Cl)Cl.O.CCOC(C)=O>[CH2:2]([O:4][C:5](=[O:16])[C@H:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[NH:7][C:17]([O:20][C:9]([CH3:14])([CH3:10])[CH3:8])=[O:18])[CH3:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 2724939Tyrosine ethyl ester hydrochloride

Product 1

HCID 11077750Ethyl N-(tert-butoxycarbonyl)-L-tyrosinateYield 180.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a mixture of L-tyrosine ethyl ester hydrochloride (55.08 g) and NaHCO3 (22.52 g) in CH2Cl2/H2O (280 ml/280 ml) was added di-tert-butyl bicarbonate (56.82 g) portionwise. The mixture was stirred for 2 hours at room temperature and diluted with AcOEt. The organic layer was washed with H2O, dried (Na2SO4) and evaporated. The residue was recrystallized from a mixture of diethyl ether and hexane to yield N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester (62.71 g). mp. 87-88° C.; MS(APCI) m/z 327(M+NH4), 310(M+H).

Workup

  1. washThe organic layer was washed with H2O
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was recrystallized from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-c8274991ad464f84a60a0d3856d7848e
Source dataset
uspto-grants-2011_01
Patent number
US07872151B2

Linked notes

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