5-(Oxiran-2-yl)-2,1,3-benzoxadiazole → 5-[(1R)-2-{4-[(2R)-2-(2,1,3-benzoxadiazol-5-yl)-2-hydroxyethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 1187161Notes

Reaction equation

HRID 1187161 reaction equation
[OH:1][C@H:2]([C:10]1[CH:19]=[CH:18][C:13]2[C:14](=[O:17])[O:15][CH2:16][C:12]=2[C:11]=1[CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[O:21]1[CH2:23][CH:22]1[C:24]1[CH:32]=[CH:31][C:27]2=[N:28][O:29][N:30]=[C:26]2[CH:25]=1>>[N:28]1[O:29][N:30]=[C:26]2[CH:25]=[C:24]([C@@H:22]([OH:21])[CH2:23][N:7]3[CH2:8][CH2:9][N:4]([CH2:3][C@@H:2]([C:10]4[CH:19]=[CH:18][C:13]5[C:14](=[O:17])[O:15][CH2:16][C:12]=5[C:11]=4[CH3:20])[OH:1])[CH2:5][CH2:6]3)[CH:32]=[CH:31][C:27]=12

Participants

3

Reactant 2

HCID 595686615-(Oxiran-2-yl)-2,1,3-benzoxadiazoleHCID 595687285-[(1R)-1-hydroxy-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 595687255-[(1R)-2-{4-[(2R)-2-(2,1,3-benzoxadiazol-5-yl)-2-hydroxyethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

Procedure

The title compounds were prepared as described for the synthesis of EXAMPLES 57-58 starting from 5-[(1R)-1-hydroxy-2-(piperazin-1-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one and 5-(oxiran-2-yl)-2,1,3-benzoxadiazole. The resulting two diastereomers were resolved by prep SFC on Chiralcel OJ 30×200 mm column eluting with 70 mL/min of 30% methanol (0.2% DEA)/CO2 at 35° C. with pressure of 100 bar.

Workup

  1. washeluting with 70 mL/min of 30% methanol (0.2% DEA)/CO2 at 35° C. with pressure of 100 bar

Sources & evidence

ORD record
ord-ad3c171e786b4748bcfb4cb0364924fd
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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