Sodium Hydroxide → 2-(1-carboxy-3-phenylpropylamino)-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid

HRID 1981120Notes

Reaction equation

HRID 1981120 reaction equation
[NH2:1][CH:2]1[CH2:13][N:5]2[CH2:6][CH2:7][CH2:8][CH:9]([C:10]([OH:12])=[O:11])[N:4]2[C:3]1=[O:14].O=[C:16]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17]([OH:19])=[O:18].[OH-].[Na+].C([BH3-])#N.[Na+]>O>[C:17]([CH:16]([NH:1][CH:2]1[CH2:13][N:5]2[CH2:6][CH2:7][CH2:8][CH:9]([C:10]([OH:12])=[O:11])[N:4]2[C:3]1=[O:14])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 697322-Oxo-4-phenylbutyric acidHCID 5003444Sodium cyanoborohydrideHCID 13341551HCID 13341551, compound

Product 1

HCID 212738942-(1-carboxy-3-phenylpropylamino)-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acidYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.51 g of 2-amino-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid (racemate B) was dissolved in 4 ml of water. 1.37 g of 2-oxo-4-phenylbutyric acid were added and the mixture was adjusted to pH 6 using 2N aqueous sodium hydroxide solution. 0.33 g of sodium cyanoborohydride was then added and the mixture was left to stir at room temperature for 22 hours. The product was absorbed on to a strong acidic ion-exchange resin and eluted with water containing 2% pyridine to give 0.62 g of crude product. Crystallization from water gave 0.3 g (32%) of 2-(1-carboxy-3-phenylpropylamino)-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid (2 racemates: racemates C and D) in the form of a white solid.

Workup

  1. waitthe mixture was left
  2. customThe product was absorbed on to a strong acidic ion-exchange resin
  3. washeluted with water containing 2% pyridine
  4. customto give 0.62 g of crude product
  5. customCrystallization from water

Sources & evidence

ORD record
ord-7c2d7d7519884723964d6bce67ae0045
Source dataset
uspto-grants-1985_04
Patent number
US04512924

Reaction notes

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