HCID 15614943, compound → HCID 15614940, compound

HRID 620351Notes

Reaction equation

HRID 620351 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[C:8]=2[C:12]([F:15])([F:14])[F:13])[C:3]=1[C:18]([N:20]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19]>C(O)=O.O>[CH2:32]([O:31][C:29]([N:20]([C:18]([C:3]1[C:4]2[C:9](=[C:8]([C:12]([F:13])([F:15])[F:14])[C:7]([O:16][CH3:17])=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[F:1])=[O:19])[CH2:21][C:22]([OH:24])=[O:23])=[O:30])[CH3:33]

Participants

4

Reactant 1

HCID 15614943HCID 15614943, compound

Product 1

HCID 15614940HCID 15614940, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of N-[[2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(ethoxycarbonyl)glycine, 1,1-dimethylethyl ester (2.40 g, 5.07 mmol) in formic acid (90 mL) was stirred at room temperature under a dry nitrogen atmosphere. After 10 minutes, dissolution occurred. After 11/2 hours, the reaction solution was diluted with water (1 L). The resultant suspension was stirred rapidly for 45 minutes, then filtered. The solid was washed with water (3×20 mL), air dried, and recrystallized from benzene:petroleum ether to provide the title compound as white needles (1.21 g, 57%), m.p. 135.5°-138° C.

Workup

  1. dissolutiondissolution
  2. filtrationfiltered
  3. washThe solid was washed with water (3×20 mL), air
  4. customdried
  5. customrecrystallized from benzene

Sources & evidence

ORD record
ord-a62b4a8f03924ae8b92957579bb68035
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

Loading…