Sodium Hydroxide → HCID 11245161, compound

HRID 1432329Notes

Reaction equation

HRID 1432329 reaction equation
C[O:2][C:3](=[O:37])[C:4]#[C:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=2)[N:8](S(C2C=CC=CC=2)(=O)=O)[CH:7]=1.[OH-].[Na+]>CCO>[O:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[C:14]2[C:6]([C:5]#[C:4][C:3]([OH:37])=[O:2])=[CH:7][NH:8][C:9]2=[N:10][CH:11]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86613121HCID 86613121, compound

Product 1

HCID 11245161HCID 11245161, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ester 14 (30 mg, 0.059 mmol), EtOH (593 μL) and 10% aq. NaOH (296 μL) was heated at 90° C. for 1 h. The reaction mixture was cooled, concentrated and acidified to pH 5 with 1N HCl. The mixture was then extracted with ethyl acetate (4×10 mL). The combined organic extracts were dried (MgSO4) and concentrated to give the crude product 15 (23 mg, 110%) which was used for the subsequent reactions without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. extractionThe mixture was then extracted with ethyl acetate (4×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ab4888106344c0fbb2338519f993936
Source dataset
uspto-grants-2009_11
Patent number
US07612086B2

Reaction notes

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