Ammonia → L-Homocysteine, N-methyl-S-(triphenylmethyl)-

HRID 1443307Notes

Reaction equation

HRID 1443307 reaction equation
[CH3:1][NH:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][S:6]C.N.CO.C(=O)=O.[Na].[Cl-].[NH4+].[C:20]1([C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][S:6][C:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 7

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 6457TriphenylcarbinolHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 6451891L-Methionine, N-methyl-HCID 21973728Carbon dioxide methanol

Product 1

HCID 10216033L-Homocysteine, N-methyl-S-(triphenylmethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.5 g (0.046 mol) of N-methyl-L-methionine is introduced, and 200 ml of ammonia is condensed while being cooled with MeOH/dry ice. At −35° C., 5.2 g (0.23 mol) of sodium is added in portions over one hour and stirred for two more hours. Then, 9.7 g (0.18 mol) of ammonium chloride is added in portions, the cooling is withdrawn, and the ammonia is driven off overnight with nitrogen. 14.0 g (0.054 mol) of triphenylmethanol is added. While being cooled with ice, 50 ml of dichloromethane and 90 ml of trifluoroacetic acid are then added. It is stirred for one hour at room temperature and evaporated to the dry state. The residue is suspended in 200 ml of water and brought to pH 13 with sodium hydroxide solution. After one more hour of stirring, it is suctioned off, and the solid is suspended in 500 ml of water. By adding citric acid, it is set at pH 4. 600 ml of MTBE is added and stirred for 30 minutes. It is suctioned off and washed twice with 100 ml each of MTBE. The residue is mixed with 100 ml of dichloromethane, 20 ml of ethanol is added, and then 500 ml of MTBE is added in drops. It is stirred for one more hour, suctioned off, washed with MTBE. After drying, 12.6 g (0.032 mol, 70% of theory) of a colorless solid is obtained.

Workup

  1. customcondensed
  2. customthe cooling is withdrawn
  3. additionare then added
  4. stirringIt is stirred for one hour at room temperature
  5. customevaporated to the dry state
  6. stirringAfter one more hour of stirring
  7. additionBy adding citric acid, it
  8. addition600 ml of MTBE is added
  9. stirringstirred for 30 minutes
  10. washwashed twice with 100 ml each of MTBE
  11. additionThe residue is mixed with 100 ml of dichloromethane, 20 ml of ethanol
  12. additionis added
  13. addition500 ml of MTBE is added in drops
  14. stirringIt is stirred for one more hour
  15. washwashed with MTBE
  16. customAfter drying
  17. custom12.6 g (0.032 mol, 70% of theory) of a colorless solid is obtained

Sources & evidence

ORD record
ord-a7b6126c001948cba7f884818c5d1db1
Source dataset
uspto-grants-2010_02
Patent number
US07659364B2

Reaction notes

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