Methanol → 3-[4-(3-Thienyl)phenyl]-alanine methyl ester

HRID 1957026Notes

Reaction equation

HRID 1957026 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[CH:8][CH:7]=2)=[CH:2]1.S(Cl)(Cl)=O.[CH3:22]O>>[CH3:22][O:16][C:15](=[O:17])[C@H:13]([CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[CH:11][CH:10]=1)[NH2:14]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 537748243-[4-(3-Thienyl)phenyl]alanine

Product 1

HCID 572132553-[4-(3-Thienyl)phenyl]-alanine methyl ester

Procedure

A solution of 3-[4-(3-thienyl)phenyl]alanine in methanol (2 ml) is slowly added to a solution of thionyl chloride (6.8 ml, 94 mmol) in methanol (5 ml) at -10° C. The mixture is slowly warmed to room temperature, then refluxed overnight. The reaction mixture is concentrated in vacuo, diluted with ethyl acetate (10 ml), and extracted with water (10 ml×3). The aqueous layer is made basic with sodium bicarbonate and extracted with ethyl acetate (10 ml×3). The organic layer is dried over magnesium sulfate and concentrated in vacuo to give a crude 3-[4-(3-thienyl)phenyl]-alanine methyl ester.

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additiondiluted with ethyl acetate (10 ml)
  4. extractionextracted with water (10 ml×3)
  5. extractionextracted with ethyl acetate (10 ml×3)
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d86fced3ea514763b5d2c46355021531
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

Loading…