HCID 67100235, compound → HCID 57983463, compound

HRID 1868777Notes

Reaction equation

HRID 1868777 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[F:17])[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:18])[C:6]([C:19]([NH:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])=[C:5]2[OH:30]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[F:17])[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:18])[C:6]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[C:5]2[OH:30]

Participants

3

Reactant 1

HCID 67100235HCID 67100235, compound

Product 1

HCID 57983463HCID 57983463, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((6,7-difluoro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (152 mg, 359 μmol) was dissolved in TFA at ambient temperature for 30 minutes and then concentrated, precipitated with hexanes, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (115 mg) as a white solid. MS (m/z)=368 (M+H)+. Calculated for C17H15F2NO6 367.09.

Workup

  1. concentrationconcentrated
  2. customprecipitated with hexanes
  3. filtrationfiltered
  4. washwashed with hexanes
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-438790749c3a47f7b83dbddf9425d9a5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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