L-Tryptophan → Methyl tryptophanate hydrochloride

HRID 2206970Notes

Reaction equation

HRID 2206970 reaction equation
O=S(Cl)[Cl:3].[OH-].[Na+].[NH2:7][C@H:8]([C:19]([OH:21])=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.[CH:22]1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>C(O)C.CO>[ClH:3].[CH3:22][O:20][C:19](=[O:21])[C@H:8]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[NH2:7]

Participants

7

Reactant 4

HCID 6305L-TryptophanHCID 10236NinhydrinHCID 14798Sodium HydroxideHCID 24386Thionyl Chloride

Product 1

HCID 2734891Methyl tryptophanate hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
66 °C

Procedure

Under ice bath, 100 ml round-bottom flask was added with 60 ml of methanol, and then slowly added with 4 ml of SOCl2 through constant pressure dropping funnel (with a drying tube on the top), and NaOH solution was used to absorb exhaust. After stirring for 1 h, 8 mmol of L-tryptophan (3d) was added and stirred at room temperature for 30 min, and then refluxed at 66° C. for 6 h. The reaction was tracked by TLC until the raw material disappears, with a solution of 2% ninhydrin in ethanol as chromogenic reagent. The solvent was evaporated out to obtain L-tryptophan methyl ester hydrochloride. Yield: 100%.

Workup

  1. customto absorb exhaust
  2. stirringstirred at room temperature for 30 min
  3. customThe solvent was evaporated out

Sources & evidence

ORD record
ord-ee6524dfe95846dd9c62e491195a7343
Source dataset
uspto-grants-2016_06
Patent number
US09376382B2

Reaction notes

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