Sodium Hydroxide → HCID 66815743, compound

HRID 2367925Notes

Reaction equation

HRID 2367925 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[N:24]=[C:23]([C:25]([O:27]C)=[O:26])[CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[N:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70206537HCID 70206537, compound

Product 1

HCID 66815743HCID 66815743, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 8 (840 mg, 2.1 mmol, 1 eq.) in methanol (5 mL) was added NaOH (168 mg, 4.2 mmol, 2 eq.) dissolved in a minimum amount of water. The mixture was stirred at room temperature and monitored by TLC. After completion of the reaction volatiles were removed in vacuo and ethyl acetate added. The solution was washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4 and concentrated in vacuo to give 810 mg of crude compound 9, which was used directly in the next step. MS m/z 386 [M+H]+

Workup

  1. customAfter completion of the reaction volatiles
  2. customwere removed in vacuo and ethyl acetate
  3. additionadded
  4. washThe solution was washed with NaH2PO4 buffer (pH 5, 1M) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6d8534402f648179964be1837f7fefb
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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