Methanol → Z-Tyr(3-tBu)-H

HRID 1988262Notes

Reaction equation

HRID 1988262 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](OC)=[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.[H-].C([Al+]CC(C)C)C(C)C.CO>C1COCC1>[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]([CH:15]=[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

5

Reactant 3

HCID 887MethanolHCID 155494893-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 87606131Z-Tyr(3-tBu)-HYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Z-Tyr(3-tBu)-OMe (3.30 g, 8.57 mmol) in THF (200 ml), diisobutyl aluminum hydride (1.0 M toluene solution) (42.9 ml, 42.9 mmol) was added dropwise at −78° C. over 15 min. After stirring for 1 hour, the mixture was mixed with methanol and a saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:2), giving the titled compound (2.18 g, 72%).

Workup

  1. extractiona saturated aqueous NaHCO3 solution and extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-01e268a12bad4d5390c90c747e80095b
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

Loading…