Sodium Hydroxide → HCID 67350552, compound

HRID 1672784Notes

Reaction equation

HRID 1672784 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]([CH:25]=[CH:26][CH:27]=3)[C:20]([O:22]CC)=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:28]=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]([CH:25]=[CH:26][CH:27]=3)[C:20]([OH:22])=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67350220HCID 67350220, compound

Product 1

HCID 67350552HCID 67350552, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl (S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoate (1.85 g, 4.64 mmol) obtained in Step 1 of Example 18 was dissolved in ethanol (23 mL), and the mixture was stirred at 90° C. for 1 hour after adding a 10% aqueous sodium hydroxide solution (1.7 mL, 46.4 mL). After concentrating the mixture under reduced pressure, a 10% aqueous hydrochloric acid solution was added and stirred. The precipitated solid was filtered off and dried to give (S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid (1.36 g, 79%).

Workup

  1. concentrationAfter concentrating the mixture under reduced pressure
  2. additiona 10% aqueous hydrochloric acid solution was added
  3. stirringstirred
  4. filtrationThe precipitated solid was filtered off
  5. customdried

Sources & evidence

ORD record
ord-ed67101ce7be42a985d7e40e88adf40f
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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