Methanol → HCID 178419105, compound

HRID 1587594Notes

Reaction equation

HRID 1587594 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[ClH:14].[NH2:1][C@H:2]([C:9]([O:11][CH3:16])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178419078HCID 178419078, compound

Product 1

HCID 178419105HCID 178419105, compound

Procedure

To a stirred solution (ice-bath) of L-histidine (38.75 g, 240 mmol) in methanol (500 ml), thionyl chloride (27.2 ml, 375 mmol) was added dropwise. After fifteen minutes the ice bath was removed and the reaction mixture was stirred at room temperature for one hour. Then after refluxing for 48 hours, it was concentrated in vacuo. The separated crystals were filtered using methanol for washing (48.93 g). The methanolic solution on dilution with ether afforded additional 10 g of the title A compound, m.p. 208°-209°, [α]D =+10.1° (c=1.8, H2O).

Workup

  1. customAfter fifteen minutes the ice bath was removed
  2. temperatureThen after refluxing for 48 hours
  3. concentrationit was concentrated in vacuo
  4. filtrationThe separated crystals were filtered
  5. washfor washing (48.93 g)
  6. customA compound, m.p. 208°-209°, [α]D =+10.1° (c=1.8, H2O)

Sources & evidence

ORD record
ord-d7a361953b1247ceb4e6636de429cab0
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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