Sodium Hydroxide → HCID 67348673, compound

HRID 1672824Notes

Reaction equation

HRID 1672824 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:24][CH:25]=[C:26]([C:28]([O:30]C)=[O:29])[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1.[OH-].[Na+]>C(O)C>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67348230HCID 67348230, compound

Product 1

HCID 67348673HCID 67348673, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl (S)-2-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxylate (172 mg, 0.381 mmol) obtained in Step 2 of Example 123 was dissolved in ethanol (3 mL), and the mixture was stirred at room temperature for 1.5 hours after adding a 2 mol/L aqueous sodium hydroxide solution (1.90 mL, 3.81 mmol). The mixture was concentrated, diluted with water, and neutralized with 1 mol/L hydrochloric acid. The precipitated solid was then filter off, and dried overnight under reduced pressure to give (S)-2-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxylic acid (110 mg, 66%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. filtrationThe precipitated solid was then filter off
  4. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-4332e33d298047d4bbb6631d696c40d6
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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