Sodium Hydroxide → HCID 25028925, compound

HRID 1644784Notes

Reaction equation

HRID 1644784 reaction equation
C([O:9][CH2:10][C@H:11]([C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=1)[O:12][C@H:13]1[CH2:21][CH2:20][C@H:19]2[C@@H:15]([CH2:16][N:17]([C:22]3[O:23][CH2:24][C:25](=[O:27])[N:26]=3)[CH2:18]2)[C@@H:14]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO.CCOCC>[F:47][C:45]([F:46])([F:48])[C:37]1[CH:36]=[C:35]([C@H:11]([O:12][C@H:13]2[CH2:21][CH2:20][C@H:19]3[C@@H:15]([CH2:16][N:17]([C:22]4[O:23][CH2:24][C:25](=[O:27])[N:26]=4)[CH2:18]3)[C@@H:14]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH2:10][OH:9])[CH:40]=[C:39]([C:41]([F:42])([F:44])[F:43])[CH:38]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71764073HCID 71764073, compound

Product 1

HCID 25028925HCID 25028925, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of benzoate of Step D (4.0 g, 5.93 mmol) in 200 mL of methanol was added 6.0 mL of 2 M sodium hydroxide. The reaction mixture was maintained at ambient temperature for 1 hr, and diluted with 1200 mL ether. The organic layer was washed with 1 M sodium hydroxide (400 mL). The organic layer was then washed with water, dried over MgSO4, filtered, and concentrated to afford a white solid. The crude material was purified by flash chromatography (0-5% then 5-7% them 7% methanol in ethyl acetate. M++1: 571.2.

Workup

  1. washThe organic layer was washed with 1 M sodium hydroxide (400 mL)
  2. washThe organic layer was then washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a white solid
  7. customThe crude material was purified by flash chromatography (0-5%

Sources & evidence

ORD record
ord-bb8c804f251746cfa62385245e0ace4b
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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