Potassium Carbonate → N-(2-fluoro-4-methylphenyl)valine

HRID 648256Notes

Reaction equation

HRID 648256 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].O(C1C=C(C=CC=1)CBr)C1C=CC=CC=1.[OH-].[Na+].CCOCC>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C@H:10]([C:11]([OH:13])=[O:12])[CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 20482718alpha-(2-Fluoro-4-methylphenylamino)isovaleric acidHCID 86719931NaOH ether

Product 1

HCID 54059120N-(2-fluoro-4-methylphenyl)valine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a mixture of 5.15 mmole of α-(2-fluoro-4-methylphenylamino)isovaleric acid, potassium carbonate (6.44 mmole), 4 ml of HMPT and 3 ml of THF, stirred, is added 5.13 mmole of m-phenoxybenzyl bromide. The reaction is stirred overnight at RT. The reaction is poured into 5% sodium hydroxide/ether, extracted with water (2×) and then washed with water (2×), dried over sodium sulfate and rotoevaporated under vacuum. The crude product is subjected to preparatory TLC eluting with 10% ether/hexane to give m-phenoxybenzyl ester of N-(2-fluoro-4-methylphenyl)valine.

Workup

  1. stirringThe reaction is stirred overnight at RT
  2. extractionextracted with water (2×)
  3. washwashed with water (2×)
  4. dry with materialdried over sodium sulfate
  5. washeluting with 10% ether/hexane

Sources & evidence

ORD record
ord-94c67970570446f380dfa6497a4936ed
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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