Potassium Permanganate → HCID 11796530, compound

HRID 2393809Notes

Reaction equation

HRID 2393809 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:27]([CH3:29])[CH3:28])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([NH:16][CH:17]([CH:21]([OH:26])[C:22]([F:25])([F:24])[F:23])[CH:18]([CH3:20])[CH3:19])=[O:15])=[O:8])=[O:4].[Mn]([O-])(=O)(=O)=O.[K+]>CO>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:27]([CH3:29])[CH3:28])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([NH:16][CH:17]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:18]([CH3:20])[CH3:19])=[O:15])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 10693669HCID 10693669, compound

Product 1

HCID 11796530HCID 11796530, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

Using a similar oxidation procedure to that described in Example 2, but using (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)propyl]-pyrrolidine-2-carboxamide and adding the potassium permanganate solution at 5°-10° C. and then stirring at 10° C. for one hour prior to treatment with methanol, there was obtained (after work-up by extration into tert-butyl methyl ether, followed by washing with brine and concentration in vacuo) (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoroacetyl)propyl]-pyrrolidine-2-carboxamide as a gum (in 75% yield); SSS:SSR ratio of 53:47; hydrate:ketone 1:1; 1H NMR similar to that of the product of Example 1. [Using a similar procedure, but adding the potassium permanganate solution at ambient temperature instead of 5°-10° C., the product was obtained in a ratio of SSS:SSR of 47:53.]

Sources & evidence

ORD record
ord-d5081997fa3943b1abbe15a2f9067e9c
Source dataset
uspto-grants-1998_09
Patent number
US05808097

Reaction notes

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