Glutaraldehyde → HCID 70416287, compound

HRID 649381Notes

Reaction equation

HRID 649381 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([NH:14][C@@H:15]1[C:21](=[O:22])[N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]2[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=2[S:17][CH2:16]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH:33](=O)[CH2:34][CH2:35][CH2:36][CH:37]=O.C([BH3-])#N.[Na+].[Cl-].[Na+]>C(O)C.O>[ClH:1].[ClH:1].[CH2:12]([O:11][C:9]([CH:8]([NH:14][C@@H:15]1[C:21](=[O:22])[N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]2[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=2[S:17][CH2:16]1)[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:10])[CH3:13]

Participants

7

Reactant 4

HCID 3485GlutaraldehydeHCID 5234Sodium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 70416887HCID 70416887, compound

Product 1

HCID 70416287HCID 70416287, compoundYield 147%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 5 ml of ethanol is dissolved 60 mg of ethyl 3(R)-(5-amino-1-ethoxycarbonylpentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate.dihydrochloride, and 0.5 g of 25% aqueous glutaraldehyde solution and 0.3 g of sodium cyanoborohydride are added to the solution, followed by stirring at room temperature for 2 hours. Water (50 ml) is added to the reaction solution, followed by adding sodium chloride to saturate the solution. The solution is extracted twice with 30 ml of ethyl acetate, and the extract is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily material is dissolved in a small amount of ethyl ether, and 0.2 ml of 5N hydrogen chloride-ethyl acetate solution is added to the solution to give 50 mg of ethyl 3(R)-(1-ethoxycarbonyl-5-piperidinopentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate.dihydrochloride as a colorless powder.

Workup

  1. additionare added to the solution
  2. concentrationto saturate the solution
  3. extractionThe solution is extracted twice with 30 ml of ethyl acetate
  4. washthe extract is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe resulting oily material is dissolved in a small amount of ethyl ether, and 0.2 ml of 5N hydrogen chloride-ethyl acetate solution
  8. additionis added to the solution

Sources & evidence

ORD record
ord-2d3da23fbda24822a301b6bd43a4e17a
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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