HCID 13273325, compound → HCID 20468454, compound

HRID 1903245Notes

Reaction equation

HRID 1903245 reaction equation
[F:1][CH:2]([F:31])[C:3]([CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])(C(OC(C)(C)C)=O)[C:4]([O:6]C(C)(C)C)=[O:5]>FC(F)(F)C(O)=O.C(O)(=O)C>[F:31][CH:2]([F:1])[CH:3]([CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 13273325HCID 13273325, compound

Product 1

HCID 20468454HCID 20468454, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-Difluoromethyl-2-(2-phthalimidoethyl)-propanedioic acid, bis tert.-butyl ester prepared as in Step B (0.610 g, 1.40 mM) is dissolved in trifluoroacetic acid (8 ml) at room temperature. After stirring for 1.5 hour at room temperature, the solvent is evaporated in vacuo yielding a white solid. The crude disubstituted malonic acid is dissolved in glacial acetic acid (20 ml) and the mixture is heated at 100° C. for 15 hours. The solvent is evaporated in vacuo yielding a yellowish oil. Crystallization in ether affords the required acid as a white solid (0.240 g, yield 60%). NMR (CDCl3 +CF3CO2H) 2.00-2.43 (m, 2H); 2.57-3.40 (m, 1H); 3.90 (t, JHH =7 Hz, 2H); 6.03 (td, JHF =55 Hz, JHH =4 Hz, 1H); 7.58-7.95 (m, 4H).

Workup

  1. customthe solvent is evaporated in vacuo
  2. customyielding a white solid
  3. temperaturethe mixture is heated at 100° C. for 15 hours
  4. customThe solvent is evaporated in vacuo
  5. customyielding a yellowish oil
  6. customCrystallization in ether

Sources & evidence

ORD record
ord-3319996fd5694709afeec4ba63e43392
Source dataset
uspto-grants-1984_03
Patent number
US04435425

Reaction notes

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