Methanol → N-methyl-5-hydroxytryptophan methyl ester hydrochloride

HRID 2117015Notes

Reaction equation

HRID 2117015 reaction equation
[CH3:1][NH:2][C@H:3]([C:14]([OH:16])=O)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.S(Cl)([Cl:19])=[O:18].[CH3:21][OH:22]>>[ClH:19].[CH3:21][O:22][C:14](=[O:16])[C@H:3]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:18])[CH:12]=2)[NH:7][CH:6]=1)[NH:2][CH3:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 160511N-methyl-L-tryptophan

Product 1

HCID 69317065N-methyl-5-hydroxytryptophan methyl ester hydrochloride

Conditions

Temperature
60 °C

Procedure

The N-methyltryptophan derivative from above (0.711 g, 1.21 mmol) was dissolved in MeOH (10 mL) and thionyl chloride (0.6 mL) was added dropwise. The mixture was heated to 60° C. for 3 h. Volatiles were removed under reduced pressure and the residue triturated with TBME (25 mL). The precipitated white solid was collected, washed with TBME and dried to give N-methyl-5-hydroxytryptophan methyl ester hydrochloride (0.339 g): MS (ES+) m/z 249 (MH+).

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue triturated with TBME (25 mL)
  3. customThe precipitated white solid was collected
  4. washwashed with TBME
  5. customdried

Sources & evidence

ORD record
ord-7f9abb44870c4bc0ab6c48ddc6bfdfb8
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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