Ethanol → HCID 13500736, compound

HRID 346175Notes

Reaction equation

HRID 346175 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([S:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:20](O)[CH3:21]>>[ClH:3].[CH2:20]([O:18][C:17](=[O:19])[C@H:15]([CH2:14][S:13][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:16])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 10331248HCID 10331248, compound

Product 1

HCID 13500736HCID 13500736, compound

Procedure

Add thionyl chloride (2.0 ml) to absolute ethanol (25 ml) at 0°-5°. To this solution add S-phenethyl-L-cysteine (2.5 g, 1.11 mmole). Warm the resulting mixture to room temperature, and then heat at 60° for 5 hours. Concentrate the reaction mixture in vacuo, dissolve the resultant residue in dichloromethane (CH2Cl2), and concentrate the solution in vacuo. Dissolve the residue in absolute ethanol, treat with DARCO, filter and concentrate in vacuo to give the title compound, a white solid (2.90 g) m.p. 155°-156°, [α]D26 =-1.5° (MeOH).

Workup

  1. temperatureheat at 60° for 5 hours
  2. concentrationConcentrate the reaction mixture in vacuo
  3. dissolutiondissolve the resultant residue in dichloromethane (CH2Cl2)
  4. concentrationconcentrate the solution in vacuo
  5. dissolutionDissolve the residue in absolute ethanol
  6. additiontreat with DARCO
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-84690d57582e454882d6baa3a970478b
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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