HCID 15385778, compound → 3-Cyclohexyl-N-(ethanesulfonyl)-D-alanyl-L-proline

HRID 1862019Notes

Reaction equation

HRID 1862019 reaction equation
[CH2:1]([S:3]([NH:6][C@@H:7]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:5])=[O:4])[CH3:2]>C(O)C.O=[Pt]=O>[CH2:1]([S:3]([NH:6][C@@H:7]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 15385778HCID 15385778, compound

Product 1

HCID 153857793-Cyclohexyl-N-(ethanesulfonyl)-D-alanyl-L-prolineYield 80.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of EtSO2-D-Phe-Pro-OH (10 g, 28 mmol) in ethanol (300 mL) was added PtO2 (5 g). The mixture was hydrogenated using a high pressure apparatus at 4.1 bar and 20° C. for 20 h. The solution was then filtered through diatomaceous earth, and concentrated to give 8.1 g (80%) of thick oil.

Workup

  1. customat 4.1 bar and 20° C.
  2. customfor 20 h
  3. filtrationThe solution was then filtered through diatomaceous earth
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6844a83916914e52af07ee1feb2f2d80
Source dataset
uspto-grants-2003_03
Patent number
US06534650B2

Reaction notes

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