Sodium Hydroxide → HCID 90412042, compound

HRID 1522020Notes

Reaction equation

HRID 1522020 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:41][CH3:42])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14](S(C4C=CC=CC=4)(=O)=O)[C:15]([C:17]4[CH2:31][CH:20]5[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH:19]5[CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1.[OH-].[Na+]>O1CCCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:41][CH3:42])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:31][CH:20]5[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:23][CH:19]5[CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90411278HCID 90411278, compound

Product 1

HCID 90412042HCID 90412042, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 262C (˜3.93 mmol) in tetrahydrofuran (28 mL) and methanol (20 mL) was added 1M aqueous sodium hydroxide (23.61 mL, 23.61 mmol) and the mixture was stirred at 60° C. for 3 hours. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 6-15% methanol in dichloromethane to give the title compound. LC-MS: 450 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with a gradient of 6-15% methanol in dichloromethane

Sources & evidence

ORD record
ord-e82a87007d2d4a7282d30c14af3f2e4c
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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