Ethanol hexane → HCID 178446893, compound

HRID 1671650Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:20]([O:21][C:22]2[CH:23]=[N:24][C:25]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[CH:26][CH:27]=2)=[CH:19][C:9]2[NH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:12][C:8]=2[CH:7]=1.[CH3:33]CCCCC.C(O)C>>[CH2:31]([S:28]([C:25]1[N:24]=[CH:23][C:22]([O:21][C:20]2[C:6]([CH:2]([OH:1])[CH2:3][CH2:4][CH:5]=[CH2:33])=[CH:7][C:8]3[N:12]=[C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)[NH:10][C:9]=3[CH:19]=2)=[CH:27][CH:26]=1)(=[O:29])=[O:30])[CH3:32]

Participants

Reactant 2

HCID 21879635Ethanol hexane

HCID 178477638HCID 178477638, compound

Product 1

HCID 178446893HCID 178446893, compound

Procedure

1-(6-((6-(Ethylsulfonyl)pyridin-3-yl)oxy)-2-pyridin-2-yl-1H-benzimidazol-5-yl)pent-4-ene-1-ol (520 mg) obtained in Example 11 was optically resolved through an optical resolution column (CHIRALPAK OD 2 cmφ×25 cmL, by Daicel Chemical Industry, mobile phase: hexane/ethanol=1/1, flow rate: 10 ml/min) to obtain its enantiomer A (retention time, 11.7 min) and enantiomer B (retention time, 15.0 min) both as a yellow solid.

Workup

customto obtain its enantiomer A (retention time, 11.7 min) and enantiomer B (retention time, 15.0 min) both as a yellow solid

Sources & evidence

ORD record: ord-a1fc522721354f129d917630b2d6fe98
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994331B2

Reaction notes

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