Sodium Hydroxide → HCID 23722235, compound

HRID 2393605Notes

Reaction equation

HRID 2393605 reaction equation
[OH-].[Na+:2].[CH:3]([N:5]1[CH:14]([C:15]([NH:17][C:18]2([CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:19]2=[O:32])=[O:16])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]>C(O)C>[CH:3]([N:5]1[CH:14]([C:15]([NH:17][C:18]2([CH2:33][CH2:34][C:35]([O-:37])=[O:36])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:19]2=[O:32])=[O:16])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18976218HCID 18976218, compound

Product 1

HCID 23722235HCID 23722235, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.79 ml of 1N sodium hydroxide was added to 30 ml of an ethanol solution of 1.70 g of ethyl 3-[3-(2-formyl-1,2,3,4-tetrahydro-3-isoquinolinyl)carbonylamino-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]propionate. The mixture was stirred at room temperature for 4 hours. After removal of solvent, the residue was dissolved in water, washed with water with diethyl ether, made acidic with 10% hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer was further extracted with a sodium hydrogen carbonate aqueous solution. The extract was adsorbed by a nonionic adsorption resin (trade name: HP-20, produced by Mitsubishi Kasei Corporation) and eluted with water and a water-methanol (1:1) mixed solution. The eluate was lyophilized to afford 1.24 g of sodium 3-[3-(2-formyl-1,2,3,4-tetrahydro-3-isoquinolinyl)carbonylamino-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]propionate as a pale yellow powder. IR (Nujol) (cm-1): 3680 to 2400 (br) , 1710, 1660, 1610, FAB-MS (m/z): 522 (MNa+), 500 (MH+, base).

Workup

  1. customAfter removal of solvent
  2. dissolutionthe residue was dissolved in water
  3. washwashed with water with diethyl ether
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate layer was further extracted with a sodium hydrogen carbonate aqueous solution
  6. customThe extract was adsorbed by a nonionic adsorption resin (trade name: HP-20, produced by Mitsubishi Kasei Corporation)
  7. washeluted with water
  8. additiona water-methanol (1:1) mixed solution

Sources & evidence

ORD record
ord-c961b325640747f5a22ab14dd29def0d
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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