Ethyl Acetate → HCID 67352373, compound

HRID 1672779Notes

Reaction equation

HRID 1672779 reaction equation
C([O:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:12]=[C:13]([N:17]3[CH2:26][C@H:25]4[N:21]([CH2:22][CH2:23][CH2:24]4)[C:20]4[N:27]=[C:28]([NH:31][CH2:32][CH3:33])[N:29]=[CH:30][C:19]=4[C:18]3=[O:34])[CH:14]=[CH:15][CH:16]=2)=[N:8][N:7]=1)(=O)C.[OH-].[Na+].C(OCC)(=O)C>CO>[CH2:32]([NH:31][C:28]1[N:29]=[CH:30][C:19]2[C:18](=[O:34])[N:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([C:9]4[O:10][C:6]([CH2:5][OH:4])=[N:7][N:8]=4)[CH:12]=3)[CH2:26][C@H:25]3[N:21]([CH2:22][CH2:23][CH2:24]3)[C:20]=2[N:27]=1)[CH3:33]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67348151HCID 67348151, compound

Product 1

HCID 67352373HCID 67352373, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-5-[3-(5-Acetoxymethyl-1,3,4-oxadiazol-2-yl)phenyl]-9-ethylamino-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (20.0 mg, 0.0432 mmol) obtained in Step 1 was dissolved in methanol (2 mL), and the mixture was stirred at room temperature for 30 minutes after adding a 1 mol/L aqueous sodium hydroxide solution (2 mL). The mixture was diluted by addition of ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and crystallized from diisopropylether to give the title compound (Compound 48) (6.0 mg, 33%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized from diisopropylether

Sources & evidence

ORD record
ord-ff0c2666410a48d28841c1c5e41ec91f
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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