Sodium Hydroxide → HCID 10506987, compound

HRID 1645790Notes

Reaction equation

HRID 1645790 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:10]([CH:12]([CH2:19][S:20]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)(=[O:22])=[O:21])[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:35]1([CH2:34][CH2:33][N:9]([CH2:8][CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:10]([CH:12]([CH2:19][S:20]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)(=[O:21])=[O:22])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10674568HCID 10674568, compound

Product 1

HCID 10506987HCID 10506987, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-[N,N-bis(2-cyclohexylethyl)carbamoyl]-5-(2-naphthylsulfonyl)pentanoate (150 mg) in ethanol (3 ml) was added a 1N sodium hydroxide solution (0.26 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo, acidified with a dilute hydrochloric acid, extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4, and evaporated at reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 86 mg of 4-[N,N-bis(2-cyclohexylethyl)carbamoyl]-5-(2-naphthylsulfonyl)pentanoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1939071aa828466b9499604dfddf4a0e
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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