Potassium Hydroxide → HCID 136364557, compound

HRID 2351856Notes

Reaction equation

HRID 2351856 reaction equation
CO[C@H](C([O:12][CH2:13][CH2:14][C:15]1[C:23]2[CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[C:21]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:20]([CH3:38])[NH:19][C:18]=2[S:17][N:16]=1)=O)C1C=CC=CC=1.[OH-].[K+]>C(O)C>[OH:12][CH2:13][CH2:14][C:15]1[C:23]2[CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[C:21]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:20]([CH3:38])[NH:19][C:18]=2[S:17][N:16]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136364558HCID 136364558, compound

Product 1

HCID 136364557HCID 136364557, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In an argon stream, 5 ml of ethanol was added to 175 mg (0.329 mM) of (-)-ethyl 3-[2-((S)-alpha-methoxybenzylcarbonyloxy)ethyl]-6-methyl-4-(3-nitrophenyl)-4,7-dihydroisothiazolo[5,4-b]pyridine-5-carboxylate obtained in Example 55 to form a solution. While the solution was cooled with ice-sodium chloride, 7 ml of a 7% aqueous solution of potassium hydroxide was added, and the mixture was stirred at the above temperature for 5 minutes. The reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate, water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give (-)-ethyl 3-(2-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-4,7-dihydroisothiazolo[5,4-b]pyridine-5-carboxylate quantitatively.

Workup

  1. customto form a solution
  2. additionwas added
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate, water
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-719e02fd79444de195355e9dab0de138
Source dataset
uspto-grants-1989_10
Patent number
US04874760

Reaction notes

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