L-Alanyl-L-proline → HCID 22822673, compound

HRID 2418446Notes

Reaction equation

HRID 2418446 reaction equation
CC(C)CCC(=O)C(OCC)=O.N[C@H](C(N1CCC[C@H]1C(O)=O)=O)C.C([BH3-])#N.[Na+].[CH2:30]([O:32][C:33]([CH:35]([NH:41][C@H:42]([C:44]([N:46]1[CH2:53][CH2:52][CH2:51][C@H:47]1[C:48]([OH:50])=[O:49])=[O:45])[CH3:43])[CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])[CH3:31]>C(O)C>[CH2:30]([O:32][C:33]([C@@H:35]([NH:41][C@H:42]([C:44]([N:46]1[CH2:53][CH2:52][CH2:51][C@H:47]1[C:48]([OH:50])=[O:49])=[O:45])[CH3:43])[CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])[CH3:31]

Participants

6

Reactant 4

HCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydrideHCID 11564543HCID 11564543, compoundHCID 22822670HCID 22822670, compound

Product 1

HCID 22822673HCID 22822673, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 5-methyl-2-oxohexanoate (3.44 g) and L-alanyl-L-proline (0.74 g) is stirred in 15 ml of ethanol with 6 g of powdered 4A molecular sieves. Sodium cyanoborohydride (0.23 g) in ethanol is added dropwise over the course of several hours. The ethanol is then removed under vacuum, the product is absorbed on strong acid ion-exchange resin and eluted with 2% pyridine in water to yield 1.08 g. of N-(1-ethoxycarbonyl-4-methylpentyl)-L-alanyl-L-proline. A portion is purified by LH-20 chromatography for spectral analysis. The nmr is in accord with structure. The mass spectrum shows a peak at 414 (silylated molecular ion -15). Chromatography affords the desired isomer.

Workup

  1. customThe ethanol is then removed under vacuum
  2. customthe product is absorbed on strong acid ion-exchange resin
  3. washeluted with 2% pyridine in water
  4. customto yield 1.08 g
  5. customA portion is purified by LH-20 chromatography for spectral analysis
  6. customChromatography affords the desired isomer

Sources & evidence

ORD record
ord-01068c707bb64f70812ab67f991b8a67
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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