4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → HCID 71565864, compound

HRID 515125Notes

Reaction equation

HRID 515125 reaction equation
Cl.[CH:2]12[CH2:23][CH:5]([CH2:6][C@@H:7]1[NH:8][CH2:9][C@@H:10]([C:12]1[C:13]([CH3:22])=[C:14]3[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[O:16][CH2:15]3)[OH:11])[CH2:4][NH:3]2.[CH3:24][C:25]1[C:33]2[CH2:32][O:31][C:30](=[O:34])[C:29]=2[CH:28]=[CH:27][C:26]=1[C@@H:35]1[CH2:37][O:36]1>>[OH:36][C@H:35]([C:26]1[CH:27]=[CH:28][C:29]2[C:30](=[O:34])[O:31][CH2:32][C:33]=2[C:25]=1[CH3:24])[CH2:37][N:3]1[CH2:4][C@@H:5]2[CH2:23][C@H:2]1[CH:7]([NH:8][CH2:9][C@H:10]([OH:11])[C:12]1[CH:20]=[CH:19][C:18]3[C:17](=[O:21])[O:16][CH2:15][C:14]=3[C:13]=1[CH3:22])[CH2:6]2

Participants

3

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×HCID 90409764HCID 90409764, compound2×

Product 1

HCID 71565864HCID 71565864, compound

Procedure

5-{(1R)-1-Hydroxy-2-[(1S,4S)-6-{[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}-2-azabicyclo[2.2.1]hept-2-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)-2-((6S)-2-azabicyclo[2.2.1]heptan-6-ylamino)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride [INTERMEDIATE 13] and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one [INTERMEDIATE 2B].

Sources & evidence

ORD record
ord-9a4467fa49594ab0a2c971d86aec2f73
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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