Methanol → 1-Methyl-D-tryptophan methyl ester hydrochloride

HRID 11224Notes

Reaction equation

HRID 11224 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][N:6]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]([CH2:9][C@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7]1.[CH3:21]O>>[ClH:3].[CH3:21][O:13][C:12](=[O:14])[C@@H:10]([CH2:9][C:8]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:6]([CH3:5])[CH:7]=1)[NH2:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 405012Indoximod

Product 1

HCID 691516871-Methyl-D-tryptophan methyl ester hydrochloride

Procedure

Thionyl chloride (1.3 mL, 18.4 mmol) was added dropwise to a suspension of 1-methyl-D-tryptophan (2.0 g, 9.2 mmol) in MeOH (30 mL) at 0° C. under a nitrogen blanket. The resulting mixture was warmed slowly to room temperature and stirred for a total of 20 hours. The solvent was removed under reduced pressure and triturated with Et2O (20 mL). The solids were collected by vacuum filtration, then dried in a vacuum oven at 60° C. for 3 days to provide Intermediate 1 as an off-white powder, which was used without further purification (2.4 g, 96%): TLC Rf (1:2 EtOAc/CHCl3)=0.22.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customtriturated with Et2O (20 mL)
  3. filtrationThe solids were collected by vacuum filtration
  4. customdried in a vacuum oven at 60° C. for 3 days

Sources & evidence

ORD record
ord-340bd4cb505843e790e3606da1ccd98b
Source dataset
uspto-grants-2006_08
Patent number
US07098209B2

Reaction notes

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