Sodium Hydroxide → HCID 10046528, compound

HRID 1768482Notes

Reaction equation

HRID 1768482 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.[OH-].[Na+]>C1COCC1.CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:17])[CH3:18])=[O:15])[C:11]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23614744HCID 23614744, compound

Product 1

HCID 10046528HCID 10046528, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To 350 mg (0.85 mmol) of ester 19-1 in a 1:1:1 mixture of THF/MeOH/H2O was added 170 mg (4.25 mmol) of NaOH. After stirring overnight at room temperature, the reaction was quenched with 1M HCl and then extracted three times with EtOAc. The combined organic phase was washed with brine, dried over MgSO4, and concentrated to provide 24-1 as a white solid. Data for 24-1: 1HNMR (500 MHz, d6-DMSO) δ 12.0 (s, 1H), 7.5-7.1 (m, 8H), 6.2 (s, 1H), 4.95 (m, 1H), 4.7 (m, 1H), 3.0 (m, 1H), 2.75 (s, 6H), 2.45 (m, 1H), 2.2 (m, 2H) ppm. HRMS (ES) calc'd M+H for C22H22F2N2O3: 401.1671. Found: 401.1695.

Workup

  1. customthe reaction was quenched with 1M HCl
  2. extractionextracted three times with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5d1c76908b64ef8b7d3909f1c5a382c
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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