Sodium Hydroxide → HCID 13656160, compound

HRID 745907Notes

Reaction equation

HRID 745907 reaction equation
[NH2:1][CH:2]([CH2:13][CH2:14][CH:15]([OH:28])[CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=[O:8])=[O:4].[C:29]1([CH2:35][CH2:36][C:37](=O)[C:38]([OH:40])=[O:39])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[OH-].[Na+].C([BH3-])#N.[Na+]>C(O)C.O>[CH2:21]([O:20][C:18]([NH:17][CH2:16][CH:15]([OH:28])[CH2:14][CH2:13][CH:2]([NH:1][CH:37]([C:38]([OH:40])=[O:39])[CH2:36][CH2:35][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=[O:8])=[O:4])=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 697322-Oxo-4-phenylbutyric acidHCID 5003444Sodium cyanoborohydrideHCID 13656158HCID 13656158, compound

Product 1

HCID 13656160HCID 13656160, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Compound VI and 4-phenyl-2-oxobutanoic acid (5 eq) were mixed with water (10 ml) and concentrated NaOH was added to raise the pH to 7.5. Ethanol was added (10 ml) and a solution of sodium cyanoborohydride (3 eq) in ethanol (4 ml) was added dropwise over 15 hours. Dowex 50W-2X (H+) (25 cc) was added with stirring. After 1 hour, the slurry was added to a column of Dowex (50 cc), the column was washed with ethanol and water and the product was eluted with 3% pyridine in water. After concentration and purfication over an LH-20 column, freeze drying gave V.

Workup

  1. additionwas added
  2. temperatureto raise the pH to 7.5
  3. additionthe slurry was added to a column of Dowex (50 cc)
  4. washthe column was washed with ethanol and water
  5. washthe product was eluted with 3% pyridine in water
  6. concentrationAfter concentration and purfication over an LH-20 column
  7. customfreeze drying
  8. customgave V

Sources & evidence

ORD record
ord-51b405988df545b9b9bc00f2c1c973ed
Source dataset
uspto-grants-1986_07
Patent number
US04602002

Reaction notes

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