L-Alanyl-L-proline → HCID 6321214, compound

HRID 1758843Notes

Reaction equation

HRID 1758843 reaction equation
O=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:16][C@H:17]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH3:18].C([BH3-])#N.[Na+]>C(O)C.O>[CH2:6]([O:5][C:3]([CH:2]([NH:16][C@H:17]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH3:18])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 83525L-Alanyl-L-prolineHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 6321214HCID 6321214, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

Ethyl 2-oxo-4-phenylbutyrate (1.03 g) and L-alanyl-L-proline (0.19 g) are dissolved in a 1:1 ethanol-water solvent. A solution of sodium cyanoborohydride (0.19 g) in ethanol-water is added dropwise at room temperature over the course of two hours. When reaction is complete, the product is absorbed on strong acid ion-exchange resin and eluted with 2% pyridine in water. The product-rich cuts are freeze dried to give 0.25 g of crude N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline. The mass spectrum shows a molecular ion at 448 m/e for the monosilylated species. Chromatography affords the desired isomer.

Workup

  1. customWhen reaction
  2. customthe product is absorbed on strong acid ion-exchange resin
  3. washeluted with 2% pyridine in water
  4. customdried

Sources & evidence

ORD record
ord-f057e7d109f0485a92e811ec0b1cb505
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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