Sodium Hydroxide → HCID 67352389, compound

HRID 1672800Notes

Reaction equation

HRID 1672800 reaction equation
C([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[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]([S:31][CH3:32])[N:29]=[CH:30][C:19]=4[C:18]3=[O:33])[CH:12]=2)[N:7]=1)(=O)C.[OH-].[Na+]>C(O)C>[OH:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([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]([S:31][CH3:32])[N:29]=[CH:30][C:19]=4[C:18]3=[O:33])[CH:14]=[CH:15][CH:16]=2)[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67351235HCID 67351235, compound

Product 1

HCID 67352389HCID 67352389, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

(S)-{3-[3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazol-5-yl}methyl acetate (529 mg, 1.13 mmol) obtained in Step 1 was dissolved in ethanol (6.0 mL), and the mixture was stirred at 60° C. for 2 hours after adding a 3 mol/L aqueous sodium hydroxide solution (4.0 mL). After concentrating the mixture under reduced pressure, water was added to the resulting residue. The precipitated white solid was filtered off, and purified by silica gel column chromatography to give (S)-5-[3-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (234 mg, 49%).

Workup

  1. concentrationAfter concentrating the mixture under reduced pressure, water
  2. additionwas added to the resulting residue
  3. filtrationThe precipitated white solid was filtered off
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e5e5e949541147a28c51a62201c29c6a
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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