L-Tryptophan → Tryptophan butyl ester

HRID 80946

Reaction equation

HRID 80946 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.S(Cl)(Cl)=O>C(O)CCC>[CH2:13]([O:14][C:13](=[O:15])[C@H:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[NH2:1])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6305L-TryptophanHCID 24386Thionyl Chloride

Product 1

HCID 11666077Tryptophan butyl esterYield 181.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

L-Tryptophane (5 g; 24.5 mmol) and thionyl chloride (73.5 mmol; 5.3 ml) were dissolved in n-butanol (80 ml) and stirred at 100° C. over night. The product 5 precipitated after cooling to room temperature, was filtered off and washed with ice cold butanol and petrol ether. The product was dried at the oil pump, yielding 5.8 g of 5 (91%).

Workup

  1. customThe product 5 precipitated
  2. temperatureafter cooling to room temperature
  3. filtrationwas filtered off
  4. washwashed with ice cold butanol and petrol ether
  5. customThe product was dried at the oil pump

Sources & evidence

ORD record
ord-4ed8fe63fe6941eca33ae882bbf034d6
Source dataset
uspto-grants-2014_09
Patent number
US08846682B2

Linked notes

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