Sodium Carbonate → 3-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

HRID 1988229Notes

Reaction equation

HRID 1988229 reaction equation
[NH2:1][C@H:2]([C:15]([O:17][CH3:18])=[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.C(=O)([O-])[O-].[Na+].[Na+].[CH:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:32][C:33](Cl)=[O:34])=[CH:27][CH:26]=1>O1CCOCC1.O>[NH:1]([C:33]([O:32][CH2:31][C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)=[O:34])[C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:12])[CH3:13])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 15549498Tyr(3-tBu)-OMe

Product 1

HCID 155494893-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Tyr(3-tBu)-OMe (41.4 g, 0.165 mol) in 1,4-dioxane (170 ml) and H2O (170 ml), under cooling with ice, sodium carbonate (26.2 g, 0.247 mol) was added and then Z—Cl (24.7 ml 0.173 mol) was further added over 25 min., followed by stirring for 2.5 hours at room temperature. The reaction mixture was mixed with water, extracted with chloroform, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure. The thus precipitated crystals were collected by filtration, washed with n-hexane and dried to give Z-Tyr(3-t-Bu)-OMe (54.7 g, 86%).

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under reduced pressure
  6. filtrationThe thus precipitated crystals were collected by filtration
  7. washwashed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-6d90af75e279477faa65c3d97b1a05c4
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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