N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(methoxycarbonyl)glycine, 1,1-Dimethylethyl Ester → 2-[N-Methoxycarbonyl-N-[[2-(2,2,2-trifluoroethoxy)-6-methoxy-5-trifluoromethyl-1-naphthalenyl]carbonyl]amino]acetic acid

HRID 620360Notes

Reaction equation

HRID 620360 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:34]([F:37])([F:36])[F:35])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([N:15]([C:24]([O:26][CH3:27])=[O:25])[CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[O:14])=[C:8]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[CH:7]=[CH:6]2>C(O)=O.O>[CH3:1][O:2][C:3]1[C:4]([C:34]([F:35])([F:37])[F:36])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([N:15]([C:24]([O:26][CH3:27])=[O:25])[CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[C:8]([O:28][CH2:29][C:30]([F:31])([F:32])[F:33])[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 15614946N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(methoxycarbonyl)glycine, 1,1-Dimethylethyl Ester

Product 1

HCID 156149412-[N-Methoxycarbonyl-N-[[2-(2,2,2-trifluoroethoxy)-6-methoxy-5-trifluoromethyl-1-naphthalenyl]carbonyl]amino]acetic acidYield 79%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of N-[[6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(methoxycarbonyl)glycine, 1,1-dimethylethyl ester (5.86 g, 10.9 mmol) in formic acid (135 mL) was stirred at room temperature under a dry nitrogen atmosphere. After 10 minutes, dissolution occurred. After 1 hour, the reaction mixture was diluted with water (1.5 L) and extracted with ether (2×400 mL). The extracts were combined and the ether was removed. The residue was suspended in water (100 mL) and filtered. The solid was washed with water (2×20 mL) and air dried. The crude product was recrystallized from chloroform to provide the title compound as a white powder (4.15 g, 79%), m.p. 186°-187° C.

Workup

  1. dissolutiondissolution
  2. waitAfter 1 hour
  3. extractionextracted with ether (2×400 mL)
  4. customthe ether was removed
  5. filtrationfiltered
  6. washThe solid was washed with water (2×20 mL) and air
  7. customdried
  8. customThe crude product was recrystallized from chloroform

Sources & evidence

ORD record
ord-675761c86feb4001bec31fed2925fab7
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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