HCID 69516615, compound → HCID 58934677, compound

HRID 854901Notes

Reaction equation

HRID 854901 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([Cl:19])[CH:18]=1)[O:15][CH:14]([C:20]([F:23])([F:22])[F:21])[C:13]([C:24]([O:26]CC)=[O:25])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cl-].[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([Cl:19])[CH:18]=1)[O:15][CH:14]([C:20]([F:23])([F:21])[F:22])[C:13]([C:24]([OH:26])=[O:25])=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69516615HCID 69516615, compound

Product 1

HCID 58934677HCID 58934677, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The ester from Step 1 was hydrolyzed via a method similar to that described in Example 9z, Step 3 to give the crude product as a tacky solid. Brine was added and the mixture was extracted with EtOAc (20 mL). The EtOAc solution was dried over MgSO4, filtered and concentrated in vacuo to give the product as a yellow crystalline solid in quantitative yield: ESHRMS m/z 383.0311 (M−H, C18H11ClF3O4, Calc'd 383.0292). 1H NMR (dmso-d6/300 MHz) 13.49 (brs, 1H), 7.90 (s, 1H), 7.34-7.50 (m, 5H), 7.27 (s, 2H), 6.05 (q, 1H, J=7.2 Hz), 5.12 (s, 2H).

Workup

  1. customto give the crude product as a tacky solid
  2. extractionthe mixture was extracted with EtOAc (20 mL)
  3. dry with materialThe EtOAc solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cfe9249bd3d4517bf1d9a9ab1e60039
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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