Benzaldehyde → HCID 54457891, compound

HRID 2413738Notes

Reaction equation

HRID 2413738 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+]>C(O)C>[CH2:21]([NH:1][C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 1155826522049-75-8

Product 1

HCID 54457891HCID 54457891, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of L-alanyl-L-prolyl-L-proline (12.83 g, 9.99 m mole), benzaldehyde (5.50 g, 51.8 m mole), zeolite "3A" (20 g), and ethanol (60 ml), was stirred overnight at room temperature. Sodium borohydride (1.609 g, 42.3 m mole) - ethanol (70 ml) suspending solution was added dropwise thereto, and after that, the mixture was stirred for 10 hours. The zeolite was removed by filtration and the filtrate was concentrated under reduced pressure. To the solution, ether was added to effect crystallization. The thus produced crystals were obtained by filtration, washed with three 50 ml portions of ether, then purified with the ion exchange resin "Dowex 50 W-X4", and then recrystallized with ethanol-ether to give N-benzyl-L-alanyl-L-prolyl-L-proline (2.10 g).

Workup

  1. additionwas added dropwise
  2. stirringafter that, the mixture was stirred for 10 hours
  3. customThe zeolite was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the solution, ether was added to effect crystallization
  6. customThe thus produced crystals were obtained by filtration
  7. washwashed with three 50 ml portions of ether
  8. custompurified with the ion exchange resin "Dowex 50 W-X4"
  9. customrecrystallized with ethanol-ether

Sources & evidence

ORD record
ord-6990ea48775d4abca3db7832992475ee
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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