Sodium Hydroxide → HCID 178453957, compound

HRID 278609Notes

Reaction equation

HRID 278609 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([Cl:36])[CH:32]=4)[CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH:18]2[C:37]([O:39]CC)=[O:38])=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([Cl:36])[CH:32]=4)[CH:27]=3)(=[O:24])=[O:25])[CH2:19][CH:18]2[C:37]([OH:39])=[O:38])=[O:16])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470009HCID 178470009, compound

Product 1

HCID 178453957HCID 178453957, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-(trans-4-tert-butoxycarbonylaminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinecarboxylate (740 mg) in ethanol (15 ml) was added 1 N sodium hydroxide solution (10 ml), and the solution was stirred at room temperature for 15 hours. The reaction solution was concentrated, and the residue was dissolved in water, adjusted to pH 2 with 1 N hydrochloric acid, extracted with dichloromethane. The extract was dried and concentrated to give a colorless solid of the title compound (614 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. customThe extract was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19ff90bebca146bab32323720fff8ebb
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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