Pyridine → 3-[4-(3-Thienyl)phenyl]alanine

HRID 1957025Notes

Reaction equation

HRID 1957025 reaction equation
C([O:5][C:6](=[O:17])[C@H:7](C)[N:8]=CC1C=CC=CC=1)(C)(C)C.[S:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=2)=[CH:19]1.N1C=CC=CC=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[S:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C@@H:7]([C:6]([OH:17])=[O:5])[NH2:8])=[CH:25][CH:24]=2)=[CH:19]1

Participants

7

Reactant 5

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 13433755Tert-butyl N-benzylidenealaninateHCID 137735383-(4-(Bromomethyl)phenyl)thiophene

Product 1

HCID 537748243-[4-(3-Thienyl)phenyl]alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(phenylmethylene)alanine t-butyl ester (210 mg, 0.90 mmol), 4-(3-thienyl)phenylmethyl bromide (250 mg, 0.99 mmol), and pyridine (7 ml, 0.09 mmol) in methylene chloride (1.8 ml) are added potassium hydroxide (505 mg, 9.0 mmol) and potassium carbonate (1.24 g, 9.0 mmol). The mixture is stirred at room temperature for 2 days, then filtered and washed with methylene chloride. The filtrate and washings are concentrated in vacuo to give a crude 3-[4-(3-thienyl)phenyl]alanine as a yellow oil.

Workup

  1. filtrationfiltered
  2. washwashed with methylene chloride
  3. concentrationThe filtrate and washings are concentrated in vacuo

Sources & evidence

ORD record
ord-694e4a723e3a458da868e81014436c64
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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