Methanol → HCID 10800561, compound

HRID 985393Notes

Reaction equation

HRID 985393 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:21]=[C:20]2[C:10]([NH:11][CH:12]=[C:13]2[CH2:14][CH:15]([C:17]([OH:19])=[O:18])[NH2:16])=[CH:9][CH:8]=1.[CH3:22]O>>[CH3:22][O:18][C:17](=[O:19])[CH:15]([CH2:14][C:13]1[C:20]2[C:10](=[CH:9][CH:8]=[C:7]([O:6][CH3:5])[CH:21]=2)[NH:11][CH:12]=1)[NH2:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1198025-Methoxytryptophan

Product 1

HCID 10800561HCID 10800561, compoundYield 73%

Procedure

Thionyl chloride (1.0 mL, 13.7 mmol) was added dropwise to a slurry of 5-methoxy-DL-tryptophan (2.0 g, 8.54 mmol) in anhydrous methanol (22 mL) at 0° C. under a nitrogen blanket. The resulting solution was warmed slowly to room temperature, stirred for 17 hours, then the solvent was removed under reduced pressure. The resulting residue was dissolved in water (20 mL), neutralized with saturated NaHCO3 (10 mL), and extracted twice with methylene chloride. The combined organic layers were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide 5-methoxy-DL-tryptophan methyl ester (Intermediate 4) as a light brown solid (1.55 g, 73%): 1H NMR (300 MHz, CDCl3): δ 7.93 (bs, 1H), 7.30-7.25 (m, 1H), 7.09-7.03 (m, 1H), 6.90-6.83 (m, 1H), 3.90-3.78 (m, 4H), 3.72 (s, 3H), 3.30-3.20 (m, 1H), 3.10-2.98 (m, 1H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe resulting residue was dissolved in water (20 mL)
  3. extractionextracted twice with methylene chloride
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d42a6de5e303490cb453d497ae0d70d3
Source dataset
uspto-grants-2005_03
Patent number
US06872721B2

Reaction notes

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