m-Chloroperbenzoic acid → HCID 90310716, compound

HRID 927244Notes

Reaction equation

HRID 927244 reaction equation
[CH3:1][N:2]1[CH:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[S:16][CH3:17])[C:6]2[C:18](=[O:21])[CH2:19][CH2:20][C:5]=2[N:4]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:3]1=[O:32].ClC1C=C(C=CC=1)C(OO)=[O:38]>ClCCl>[CH3:1][N:2]1[CH:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[S:16]([CH3:17])=[O:38])[C:6]2[C:18](=[O:21])[CH2:19][CH2:20][C:5]=2[N:4]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=2)[C:3]1=[O:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90311128HCID 90311128, compound

Product 1

HCID 90310716HCID 90310716, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methylthio)benzonitrile (example 27.1, 20 mg, 0.04 mmol) in dichloromethane (3.0 mL) is treated with meta-chloroperoxybenzoic acid (77%, 10 mg, 0.04 mmol), and the mixture is stirred at room temperature for 20 min. All volatiles are removed under reduced pressure, and the residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA), whereupon the two diastereomers of 4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methylsulfinyl)benzonitrile are separated.

Workup

  1. customAll volatiles are removed under reduced pressure
  2. customthe residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA), whereupon the two diastereomers of 4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methylsulfinyl)benzonitrile
  3. customare separated

Sources & evidence

ORD record
ord-a6ca1e8d01ec4a07899c1a95054821a0
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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