Methanol → HCID 69677696, compound

HRID 584223Notes

Reaction equation

HRID 584223 reaction equation
S(Cl)([Cl:3])=O.Cl.[CH3:6][C:7]1[CH:8]=[C:9]([NH:14][C@@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[CH:10]=[CH:11][C:12]=1[CH3:13].[CH3:20]O>>[ClH:3].[CH3:20][O:18][C:17](=[O:19])[C@@H:15]([CH3:16])[NH:14][C:9]1[CH:10]=[CH:11][C:12]([CH3:13])=[C:7]([CH3:6])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 69677733HCID 69677733, compound

Product 1

HCID 69677696HCID 69677696, compound

Procedure

Thionyl chloride (5.4 ml) was added dropwise to methanol (60 ml) below 5° C. with ice-salt bath cooling and stirring was continued for 10 minutes at the same temperature. 3,4-Dimethylphenyl-D-alanine hydrochloride (5.0 g) was added to the mixture by small portions over 20 minutes at −15° C. and the whole was stirred at room temperature for 6 hours, and evaporated under reduced pressure. The resulting solid was triturated with isopropyl ether to give colorless crystals of 3,4-dimethylphenyl-D-alanine methyl ester hydrochloride (5.10 g).

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred at room temperature for 6 hours
  3. customevaporated under reduced pressure
  4. customThe resulting solid was triturated with isopropyl ether

Sources & evidence

ORD record
ord-b6db8e700fa745fb97264f458f87ea12
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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