HCID 178451286, compound → HCID 178525895, compound

HRID 1868957Notes

Reaction equation

HRID 1868957 reaction equation
[F:1][C:2]1[C:16]([F:17])=[C:15]2[C:5]([C:6](=[O:30])[C:7]([C:19]([NH:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])=[C:8]([OH:18])[C:9]32[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.O>[F:1][C:2]1[C:16]([F:17])=[C:15]2[C:5]([C:6](=[O:30])[C:7]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[C:8]([OH:18])[C:9]32[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178451286HCID 178451286, compound

Product 1

HCID 178525895HCID 178525895, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of t-butyl N-((7,8-difluoro-2-hydroxy-4-oxo-2′,3′,5′,6′-tetrahydro-4H-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (0.13 g, 0.3 mmol) in 3 mL TFA was stirred at room temperature for 1 hour. The mixture was diluted with 100 mL water and a white precipitate was formed to form a suspension. The suspension was stirred for 30 minutes at room temperature, filtered, and washed with 20 mL water. The solid was dried under vacuum at 45° C. for 15 hours to give 0.09 g of the title compound as a white solid. MS m/e: (M+H)+ 368.

Workup

  1. customa white precipitate was formed
  2. customto form a suspension
  3. stirringThe suspension was stirred for 30 minutes at room temperature
  4. filtrationfiltered
  5. washwashed with 20 mL water
  6. customThe solid was dried under vacuum at 45° C. for 15 hours

Sources & evidence

ORD record
ord-8fffa071bc2a46c3a484e01b0543999d
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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