Methanol → L-Tryptophan

HRID 2056789Notes

Reaction equation

HRID 2056789 reaction equation
[CH2:1]([N:11]=[C:12]=S)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]C.[CH3:14][OH:15].[OH2:16].C[N:18](C=O)C>>[NH2:18][C@H:9]([C:14]([OH:16])=[O:15])[CH2:8][C:7]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[NH:11][CH:12]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 90535Decane, 1-isothiocyanato-

Product 1

HCID 6305L-Tryptophan

Procedure

To a suspension of compound AA (9.1 g) in dry N,N′-dimethylformamide (15 ml) was added n-decylisothiocyanate (1.2 ml). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was poured on to Bondesil 40 μM C8 resin (400 g) that had been prewashed with methanol (1 L) and water (1 L). The product was eluted with methanol (800 ml) after being first washed with water (800 ml) followed by 20% acetonitrile in water (800 ml). Evaporation of the methanol gave compound BB as a yellow solid (7.3 g).

Workup

  1. washThe product was eluted with methanol (800 ml)
  2. washafter being first washed with water (800 ml)
  3. customEvaporation of the methanol

Sources & evidence

ORD record
ord-efc564ca20644543b396101ebb2cd497
Source dataset
uspto-grants-2008_02
Patent number
US07335726B2

Reaction notes

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