Ammonia → Tyr(3-tBu)-NH2

HRID 1988269Notes

Reaction equation

HRID 1988269 reaction equation
[NH2:1][C@H:2]([C:15]([O:17]C)=O)[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.[NH3:19]>CO>[NH2:1][C@H:2]([C:15]([NH2:19])=[O:17])[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 222AmmoniaHCID 15549498Tyr(3-tBu)-OMe

Product 1

HCID 131722727Tyr(3-tBu)-NH2Yield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Tyr(3-tBu)-OCH3 (1.5 g, 5.97 mmol) in MeOH (10 ml), aqueous ammonia (10 ml) was added and stirred at room temperature overnight. The mixture was evaporated to remove the solvent under reduced pressure and the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:methanol=10:1), giving Tyr(3-tBu)-NH2 (1.4 g, 99%).

Workup

  1. customThe mixture was evaporated
  2. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-48d41be5153f4ef6ad93e4902fccfa89
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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