4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 5-{(1R)-1-Hydroxy-2-[3-(1-{[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}cyclobutyl)pyrrolidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one

HRID 515117Notes

Reaction equation

HRID 515117 reaction equation
Cl.[OH:2][C@H:3]([C:15]1[CH:24]=[CH:23][C:18]2[C:19](=[O:22])[O:20][CH2:21][C:17]=2[C:16]=1[CH3:25])[CH2:4][NH:5][C:6]1([CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)[CH2:9][CH2:8][CH2:7]1.[CH3:26][C:27]1[C:35]2[CH2:34][O:33][C:32](=[O:36])[C:31]=2[CH:30]=[CH:29][C:28]=1[C@@H:37]1[CH2:39][O:38]1>>[OH:38][C@H:37]([C:28]1[CH:29]=[CH:30][C:31]2[C:32](=[O:36])[O:33][CH2:34][C:35]=2[C:27]=1[CH3:26])[CH2:39][N:12]1[CH2:13][CH2:14][CH:10]([C:6]2([NH:5][CH2:4][C@H:3]([OH:2])[C:15]3[CH:24]=[CH:23][C:18]4[C:19](=[O:22])[O:20][CH2:21][C:17]=4[C:16]=3[CH3:25])[CH2:9][CH2:8][CH2:7]2)[CH2:11]1

Participants

3

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×HCID 895451635-[(1R)-1-hydroxy-2-{[1-(pyrrolidin-3-yl)cyclobutyl]amino}ethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715657205-{(1R)-1-Hydroxy-2-[3-(1-{[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}cyclobutyl)pyrrolidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one

Procedure

5-{(1R)-1-Hydroxy-2-[3-(1-{[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}cyclobutyl)pyrrolidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 1 starting from 5-[(1R)-1-hydroxy-2-{[1-(pyrrolidin-3-yl)cyclobutyl]amino}ethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride [INTERMEDIATE 5] and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one [INTERMEDIATE 2B].

Sources & evidence

ORD record
ord-1950a6dcb6f4412b97fb6706c11cbd85
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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