HCID 54181919, compound → HCID 53739668, compound

HRID 275615Notes

Reaction equation

HRID 275615 reaction equation
[CH3:1][C:2]([S:12]([CH2:15][C@@H:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])([C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5])[CH3:3].[H][H]>CO.[Rh]>[CH3:3][C:2]([S:12]([CH2:15][C@@H:16]([CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[C:17]([OH:19])=[O:18])(=[O:13])=[O:14])([C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5])[CH3:1]

Participants

5

Reactant 2

HCID 54181919HCID 54181919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53739668HCID 53739668, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 610mg (1.59mmol) (S)-α-[[[1-methyl-1-(morpholinocarbonyl)ethyl]sulfonyl]methyl]hydrocinnamic acid in 20 ml of methanol was hydrogenated in the presence of 60 mg of rhodium on aluminium oxide at 500 for 4 hours at a pressure of 106Pa of hydrogen. Subsequently, the catalyst was filtered off and rinsed with methanol. The methanolic solution was evaporated under reduced pressure, whereby 580 mg of (S)-α-[[[1-methyl-1-(morpholinocarbonyl)ethyl]sulfonyl]methyl]cyclohexanepropionic acid, MS: 346 (M-C3H7)+ were obtained as a colourless crystalline solid.

Workup

  1. filtrationSubsequently, the catalyst was filtered off
  2. washrinsed with methanol
  3. customThe methanolic solution was evaporated under reduced pressure, whereby 580 mg of (S)-α-[[[1-methyl-1-(morpholinocarbonyl)ethyl]sulfonyl]methyl]cyclohexanepropionic acid, MS
  4. custom346 (M-C3H7)+ were obtained as a colourless crystalline solid

Sources & evidence

ORD record
ord-179af9bd3b35412bbd5c82c3c8a12765
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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