cyclo(valylvalyl) → HCID 7075896, compound

HRID 926977Notes

Reaction equation

HRID 926977 reaction equation
N[C@@H](C(C)C)CO.[CH:8]([CH:11]1[NH:16][C:15](=[O:17])[CH:14]([CH:18]([CH3:20])[CH3:19])[NH:13][C:12]1=[O:21])([CH3:10])[CH3:9]>>[CH:8]([C@@H:11]1[NH:16][C:15](=[O:17])[C@H:14]([CH:18]([CH3:20])[CH3:19])[NH:13][C:12]1=[O:21])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 519728cyclo(valylvalyl)HCID 640993L-Valinol

Product 1

HCID 7075896HCID 7075896, compoundYield 78%

Procedure

Upon refluxing a dioxane solution containing 2 mmol of (2S,3S)-2-amino-3-methylpentan-1-ol and 0.02 mmol of catalyst 1 for 19 hrs and cooling the reaction mixture, the solid product precipitated and was filtered off and dried under vacuum to give pure 3-(sec-butyl)-6-(sec-butyl)piperazine-2,5-dione 7c in 72% yield (Table 9, entry 2). The structure was confirmed by NMR and MS spectroscopies. Under the same conditions, cyclic peptidation of (S)-2-amino-3-methylbutan-1-ol led to 3,6-diisopropylpiperazine-2,5-dione 7d as an insoluble solid which separated from the reaction mixture and was isolated by filtration and dried under vacuum to give 78% of (3S,6S)-3,6-diisopropylpiperazine-2,5-dione 7d (Table 9, entry 3). The optical rotation of the pure product (−52°) was essentially the same as reported in the literature (−) 54°. Thus, under these experimental condition, no racemization took place.

Workup

  1. customseparated from the reaction mixture
  2. customwas isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-842bceeac872439681501667803e71bf
Source dataset
uspto-grants-2016_03
Patent number
US09290441B2

Reaction notes

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