Acetaldehyde → N-Et-Tyr(3-tBu)-NHMe

HRID 1988293Notes

Reaction equation

HRID 1988293 reaction equation
[NH2:1][C@H:2]([C:15]([NH: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.[CH:19](=O)[CH3:20].ClCCl.[BH4-].[Na+]>O>[NH:1]([CH2:19][CH3:20])[C@H:2]([C:15]([NH: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 4

HCID 177AcetaldehydeHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 131722741Tyr(3-tBu)-NHMe

Product 1

HCID 131727522N-Et-Tyr(3-tBu)-NHMeYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Tyr(3-tBu)-NHMe (1.7 g, 6.8 mmol), acetaldehyde (0.76 ml, 13.6 mmol) and dichloromethane (10 ml) was stirred under cooling with ice for 30 min. The reaction mixture was concentrated under reduced pressure under cooling with ice; the thus obtained residue was mixed with methanol (20 ml) and then under cooling with ice with sodium borohydride (0.28 g, 7.4 mmol) and stirred at the same temperature for 15 min. The resultant was mixed with water and extracted with dichloromethane. The organic layer was washed with water, dried and concentrated under reduced pressure under cooling with ice; the thus obtained residue was subjected to silica gel column chromatography (CHCl3:MeOH=20:1), giving N-Et-Tyr(3-tBu)-NHMe (T8) (1.7 g, 90%).

Workup

  1. temperatureunder cooling with ice for 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. temperatureunder cooling with ice
  4. additionthe thus obtained residue was mixed with methanol (20 ml)
  5. stirringstirred at the same temperature for 15 min
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. temperatureunder cooling with ice

Sources & evidence

ORD record
ord-f88b4c2680744cbf8fc9fb4ed5fb2d92
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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