Hydrochloric Acid → HCID 53819108, compound

HRID 986637Notes

Reaction equation

HRID 986637 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].[F:15][C:16](=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:17](Cl)=[O:18].Cl>O.CC(C)=O>[F:15][C:16](=[CH:20][C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)[C:17]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 14798Sodium Hydroxide2×HCID 85592604HCID 85592604, compound

Product 1

HCID 53819108HCID 53819108, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

L-phenylalanine (13.2 g, 0.080 mole) and 6N NaOH (43 ml, 0.086 mole) were dissolced in a solvent prepared by mixing water (77 ml) with acetone (240 ml). To the mixture, while cooling to less than 10° C., the acetone solution of α-fluoro-4-methyl cinnamic acid chloride prepared as above and 2N NaOH (38 ml, 0.076 mole) were alternately added over 20 minutes. Next, the mixture was stirred at normal temperature for 30 minutes, and the reaction solution was made acidic by the addition of 2N HCl. Then, water (200 ml) was gradually added thereto. The thus precipitated crystals were recovered by filtration and dried to give crude crystals (16.7 g). The crude crystals were recrystallized from a mixture of methanol and water to obtain N-(α-fluoro-4-methylcinnamoyl)-L-phenylalanine (yield 15.5 g) in the form of white needle-like crystals having a melting point of 163° to 163.5° C.

Workup

  1. customprepared
  2. temperatureTo the mixture, while cooling to less than 10° C.
  3. additionwere alternately added over 20 minutes
  4. filtrationThe thus precipitated crystals were recovered by filtration
  5. customdried
  6. customto give crude crystals (16.7 g)
  7. customThe crude crystals were recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-6b0291f01ee2473eb0893c78b84757ef
Source dataset
uspto-grants-1987_12
Patent number
US04714713

Reaction notes

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