Sodium Hydroxide → 2-[7-Benzyl-2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl]pentanoic acid

HRID 1627888Notes

Reaction equation

HRID 1627888 reaction equation
[CH2:1]([N:8]1[CH2:20][C:19]2[S:18][C:17]3[N:16]=[C:15]([CH3:21])[C:14]([CH:22]([CH2:28][CH2:29][CH3:30])[C:23]([O:25]CC)=[O:24])=[C:13]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)[C:12]=3[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C(O)C>[CH2:1]([N:8]1[CH2:20][C:19]2[S:18][C:17]3[N:16]=[C:15]([CH3:21])[C:14]([CH:22]([CH2:28][CH2:29][CH3:30])[C:23]([OH:25])=[O:24])=[C:13]([C:31]4[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=4)[C:12]=3[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66597436Ethyl [7-benzyl-2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl]pentanoate

Product 1

HCID 498052482-[7-Benzyl-2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl]pentanoic acidYield 5.6%

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

To a suspension of ethyl [7-benzyl-2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl]pentanoate (0.514 g; 1 mmol) in a mixture methanol-ethanol (2:1) (15 mL) was added a 5% sodium hydroxide solution (15 mmol; 12 mL) and the reaction mixture was heated at reflux for 18 h. After cooling, the organic volatiles were removed under reduced pressure and the remaining basic solution was acidified with HCl (1N) until pH 2 and the aqueous layer was extracted with ethyl acetate. The organics were combined, dried over magnesium sulphate and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 2) furnished 0.027 g (5.5%) of the title compound as a light yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling
  4. customthe organic volatiles were removed under reduced pressure
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customPurification by preparative HPLC (HPLC method 2)

Sources & evidence

ORD record
ord-3380f1f9badf4880b1571d3652c2d585
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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