Methanol → N-(tert-Butoxycarbonyl)-O-[2-(2,6-dichloro-4-methylphenoxy)ethyl]tyrosine

HRID 561862Notes

Reaction equation

HRID 561862 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32]C)=[O:31])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Li+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([OH:32])=[O:31])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66762575Methyl N-(tert-butoxycarbonyl)-O-[2-(2,6-dichloro-4-methylphenoxy)ethyl]tyrosinate

Product 1

HCID 66761614N-(tert-Butoxycarbonyl)-O-[2-(2,6-dichloro-4-methylphenoxy)ethyl]tyrosine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl N-(tert-butoxycarbonyl)-O-[2-(2,6-dichloro-4-methylphenoxy)ethyl]tyrosinate from the previous step (1 eq.) was dissolved in a 2:1 (v/v) THF:MeOH solution (0.07 M). To this was then added lithium hydroxide (1.0 M aqueous solution, 5 eq.) and the resulting solution was stirred at RT for 16 h. The volatiles were then removed in vacuo. Following careful acidification of the resulting residue with 10% aq. HCl, the mixture was extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound.

Workup

  1. customThe volatiles were then removed in vacuo
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0c3189686b1c497b905d6e85bae01aed
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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