Methanol → HCID 86746632, compound

HRID 2255079Notes

Reaction equation

HRID 2255079 reaction equation
S(Cl)(Cl)=O.[CH3:5][C@@:6]([C:16]([OH:18])=[O:17])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:7].[CH3:19]O>>[CH3:19][O:17][C:16](=[O:18])[C@:6]([CH3:5])([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 14037832HCID 14037832, compound

Product 1

HCID 86746632HCID 86746632, compound

Procedure

430 ml methanol are cooled to -10° C. in an ice/sodium chloride mixture and reacted with 21.3 ml thionyl chloride (exothermic reaction). 44.5 g (0.23 mol) α-methyl-homo-phenylalanine are added dropwise at room temperature. Boiling under reflux occurs for 8.5 hours, the mixture is concentrated in a rotary evaporator, taken up with H2O (350 ml) and reacted with 150 ml 25% NH4OH solution. Extraction with dichloromethane occurs 5× and the combined extracts are dried over calcium carbonate and concentrated in a rotary evaporator. Yellowish oil.

Workup

  1. temperatureBoiling under reflux
  2. concentrationthe mixture is concentrated in a rotary evaporator
  3. customreacted with 150 ml 25% NH4OH solution
  4. extractionExtraction with dichloromethane
  5. dry with materialthe combined extracts are dried over calcium carbonate
  6. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-67aee71e6b9e4293ad37335e58e2539b
Source dataset
uspto-grants-1993_08
Patent number
US05238955

Reaction notes

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