HCID 67099890, compound → HCID 57983416, compound

HRID 1868791Notes

Reaction equation

HRID 1868791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[Cl: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 67099890HCID 67099890, compound

Product 1

HCID 57983416HCID 57983416, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((6,7-dichloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (350 mg, 767 μmol) was dissolved in TFA (3 mL). The resulting mixture was stirred for 1 hour and then concentrated, precipitated with hexanes, sonicated, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (268 mg, 87.3% yield) as a white solid. MS (m/z)=400 (M+H)+. Calculated for C17H15Cl2NO6 399.03.

Workup

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

Sources & evidence

ORD record
ord-20ab1a9f5a6f4c3199cd5139e62b6f87
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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