MeOH tetrahydrofuran → HCID 67486117, compound

HRID 1880572Notes

Reaction equation

HRID 1880572 reaction equation
C1COCC1.CO.[F:8][C:9]([F:40])([F:39])[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=3)[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:12]=1>O>[F:8][C:9]([F:39])([F:40])[O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[C:19]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 69308917HCID 69308917, compound

Product 1

HCID 67486117HCID 67486117, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF/MeOH solution (ca. 1/1, 2 mL) of the intermediate from Step C (40 mg, 0.09 mmol) was added LiOH monohydrate (20 mg, 0.49 mmol) in 1 mL water. The solution was stirred at room temperature until no ester remained by HPLC analysis. The solution was concentrated and partitioned between ethyl acetate and aqueous 1N HCl. The organic phase was washed with brine, dried over MgSO4 and filtered. The solution was then concentrated to give the title compound which was used without further purification. LCMS1 4.27 min. (M+H)=439

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned between ethyl acetate and aqueous 1N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe solution was then concentrated

Sources & evidence

ORD record
ord-a05248b82b724dd8bcb8a94856b27eaa
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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