L-Valine → HCID 20382854, compound

HRID 1447949Notes

Reaction equation

HRID 1447949 reaction equation
[F:1][C:2]1[C:3]([CH2:13]Br)=[C:4]([CH2:11]Br)[C:5]([F:10])=[C:6]([F:9])[C:7]=1[F:8].[NH2:15][C@H:16]([C:20]([OH:22])=[O:21])[CH:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[OH-].[K+]>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]2[C:3]=1[CH2:13][N:15]([CH:16]([CH:17]([CH3:19])[CH3:18])[C:20]([OH:22])=[O:21])[CH2:11]2

Participants

6

Reactant 4

HCID 6287L-ValineHCID 11430Potassium CarbonateHCID 13689797HCID 13689797, compoundHCID 86583969tetrahydrofuran HMPA

Product 1

HCID 20382854HCID 20382854, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 3,4,5,6-tetrafluoro-1,2-bis(bromomethyl)benzene (3 g, 9 mmol), valine (1 g, 9 mmol), potassium carbonate (2.8 g) and 25 ml THF/HMPT (1:1) is stirred for about 24 hours at RT (the reaction is followed by TLC). The reaction mixture is then diluted with 100 ml aqueous 10% KOH and extracted three times with ether. The aqueous phase is acidified to about pH 3 with aqueous HCl and extracted thoroughly with ether. The organic layer is washed with water, dried and solvent removed under vacuum to give 2-(4,5,6,7-tetrafluoro-2-isoindolinyl)-3-methylbutanoic acid.

Workup

  1. extractionextracted three times with ether
  2. extractionextracted thoroughly with ether
  3. washThe organic layer is washed with water
  4. customdried
  5. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-a5670438bcca4dfe8347329d567b4a9b
Source dataset
uspto-grants-1979_12
Patent number
US04178293

Reaction notes

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