HCID 15614949, compound → HCID 3012986, compound

HRID 620366Notes

Reaction equation

HRID 620366 reaction equation
[Br: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>[Br: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:13])[F:14])[C:3]=1[C:18]([N:20]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][C:22]([OH:24])=[O:23])=[O:19]

Participants

4

Reactant 1

HCID 15614949HCID 15614949, compound

Product 1

HCID 3012986HCID 3012986, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of N-[[2-bromo-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(ethoxycarbonyl)glycine, 1,1-dimethylethyl ester (4.68 g, 8.76 mmol) in formic acid (150 mL) was stirred at room temperature under a dry nitrogen atmosphere. After 15 minutes, dissolution occurred. After 11/4 hours, the reaction was diluted with water (1.2 L). The aqueous phase was extracted with ether (2×300 mL). The extracts were combined, dried with magnesium sulfate, and the ether was removed. The residue was suspended in water (150 mL) and filtered. The solid was washed with water (2×30 mL) and dried. The crude product was recrystallized in chloroform:hexane twice to yield the title compound as white needles (2.24 g, 53%), m.p. 167°-168.5° C.

Workup

  1. dissolutiondissolution
  2. extractionThe aqueous phase was extracted with ether (2×300 mL)
  3. dry with materialdried with magnesium sulfate
  4. customthe ether was removed
  5. filtrationfiltered
  6. washThe solid was washed with water (2×30 mL)
  7. customdried
  8. customThe crude product was recrystallized in chloroform

Sources & evidence

ORD record
ord-0abadca07c244391a4cafaffce6ff9ec
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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