Carbon Tetrachloride → N-(1-ethoxycarbonyl-3-p-chlorophenylpropyl)-L-alanyl-L-proline

HRID 2418438Notes

Reaction equation

HRID 2418438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.[NH2:22][C@H:23]([C:25]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30])=[O:26])[CH3:24].[BH3-]C#N.[Na+]>C(O)C>[CH2:14]([O:13][C:11]([CH:10]([NH:22][C@H:23]([C:25]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30])=[O:26])[CH3:24])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:12])[CH3:15]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydrideHCID 13201328Ethyl 4-(4-chlorophenyl)-2-oxobutanoate

Product 1

HCID 22822712N-(1-ethoxycarbonyl-3-p-chlorophenylpropyl)-L-alanyl-L-proline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of ethyl 4-p-chlorophenyl-2-oxobutyrate (prepared from the acid by esterification with ethanol in refluxing CCl4) and L-alanyl-L-proline in ethanol can be treated with excess NaBH3CN and stirred at room temperature until reaction is complete. The ethanol can then be removed under vacuum and the product absorbed on strong acid ion-exchange resin. By elution with 2% pyridine in water, one can obtain N-(1-ethoxycarbonyl-3-p-chlorophenylpropyl)-L-alanyl-L-proline.

Workup

  1. customThe ethanol can then be removed under vacuum
  2. customthe product absorbed on strong acid ion-exchange resin
  3. washBy elution with 2% pyridine in water, one

Sources & evidence

ORD record
ord-8b574173471349e094a827ec36219aec
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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