m-Chloroperbenzoic acid → (+-)-p-(3-(Ethyl(3-(propylsulfinyl)propyl)amino)-2-hydroxypropoxy)benzonitrile

HRID 974192Notes

Reaction equation

HRID 974192 reaction equation
[CH2:1]([N:3]([CH2:17][CH2:18][CH2:19][S:20][CH2:21][CH2:22][CH3:23])[CH2:4][C@@H:5]([OH:16])[CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:32])C=1>CO>[CH2:1]([N:3]([CH2:17][CH2:18][CH2:19][S:20]([CH2:21][CH2:22][CH3:23])=[O:32])[CH2:4][C@@H:5]([OH:16])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 150668444-[3-[ethyl[3-(propylthio)propyl]amino]-2(R)-hydroxypropoxy]benzonitrile

Product 1

HCID 15066846(+-)-p-(3-(Ethyl(3-(propylsulfinyl)propyl)amino)-2-hydroxypropoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Oxidation of 4-[3-[ethyl[3-(propylthio)propyl]amino]-2(R)-hydroxypropoxy]benzonitrile with m-chloroperbenzoic acid was carried out as described for the stereoisomeric mixture in example 3. [α]D20 -18.6° (C 1.0, CH3OH).

Sources & evidence

ORD record
ord-0cbb66ddd3ee49ae9efb25127005fbe4
Source dataset
uspto-grants-1991_11
Patent number
US05068272

Reaction notes

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