Methylamine → Tyr(3-tBu)-NHMe

HRID 1383724Notes

Reaction equation

HRID 1383724 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.[CH3:19][NH2:20].[C-]#N.[Na+]>CO>[NH2:1][C@H:2]([C:15]([NH:20][CH3:19])=[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

5

Reactant 3

HCID 6329MethylamineHCID 8929Sodium CyanideHCID 15549498Tyr(3-tBu)-OMe

Product 1

HCID 131722741Tyr(3-tBu)-NHMe

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 10.6 g (42.0 mmol) of Tyr(3-tBu)-OMe in 80 ml of methanol, 80 ml of a solution of 40% methylamine in methanol and 0.41 g of sodium cyanide were added and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in methylene chloride, followed by washing first with water, then with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 20:1:0.1) to give Tyr(3-tBu)-NHMe in the amount of 7.3 g (70%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in methylene chloride
  3. washby washing first with water
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting solvent

Sources & evidence

ORD record
ord-eaba3042d66f4b80b21192bae6d7a6fa
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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