Lithium hydroxide, monohydrate → Z-Tyr(3-tBu)-OH

HRID 1988296Notes

Reaction equation

HRID 1988296 reaction equation
[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:15]([O:17]C)=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.O.[OH-].[Li+]>CO.O>[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C@H:2]([C:15]([OH:17])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 155494893-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 131727524Z-Tyr(3-tBu)-OHYield 100.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of Z-Tyr(3-tBu)-OMe (1.01 g, 2.62 mmol) in methanol/water (12 ml/3 ml), lithium hydroxide monohydrate (0.17 g, 3.93 mmol) was added and stirred at room temperature for 2 hours. The reaction mixture was washed with ether, rendered acidic by 2N hydrochloric acid and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure, giving crude Z-Tyr(3-tBu)-OH (0.98 g).

Workup

  1. washThe reaction mixture was washed with ether
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-8a8a766cf14e425ba70672a4f35f27bb
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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