Sodium Hydroxide → HCID 115011681, compound

HRID 920788Notes

Reaction equation

HRID 920788 reaction equation
[F:1][C:2]1([CH3:12])[CH2:5][C:4]([CH3:11])([C:6]([O:8]CC)=[O:7])[CH2:3]1.[OH-].[Na+]>C(O)C>[F:1][C:2]1([CH3:12])[CH2:5][C:4]([CH3:11])([C:6]([OH:8])=[O:7])[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118061776HCID 118061776, compound

Product 1

HCID 115011681HCID 115011681, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Intermediate 307A (85 mg, 0.360 mmol) in ethanol (2 mL) was added NaOH (0.144 mL, 0.719 mmol, 5M aq. solution) and the reaction mixture was stirred at RT for 12 h. The volatiles were removed under reduced pressure, and the residue was diluted with water (15 mL) and extracted with diethyl ether (1×25 mL). The aqueous layer was then acidified with a 1.5N aq. solution of HCl and extracted with EtOAc (2×25 mL). The combined organic layer was dried over Na2SO4, filtered and the filtrate concentrated to afford Intermediate 307B as a pale yellow liquid (30 mg, 43%). 1H NMR (300 MHz, DMSO-d6) δ ppm 12.29 (br. s., 1H), 2.60-2.53 (m, 1H), 2.37-2.22 (m, 3H), 1.44 (d, J=18 Hz, 3H), 1.36 (s, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue was diluted with water (15 mL)
  3. extractionextracted with diethyl ether (1×25 mL)
  4. extractionextracted with EtOAc (2×25 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-e98eabe07eb74e38a2f6d01b2418db89
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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