(S,E)-3-(pent-2-enoyl)-4-phenyloxazolidin-2-one → 4-((4S,5S)-5-(Cyanomethyl)-4-ethyl-1-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile

HRID 2278693Notes

Reaction equation

HRID 2278693 reaction equation
[C:1](N1[C@@H](C2C=CC=CC=2)COC1=O)(=O)/C=C/CC.[C:19]([CH2:21][C@@H:22]1[N:26]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[N:25]=[C:24]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[C@H:23]1[CH3:42])#[N:20]>>[C:19]([CH2:21][C@@H:22]1[N:26]([C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)[N:25]=[C:24]([C:34]2[CH:35]=[CH:36][C:37]([C:38]#[N:39])=[CH:40][CH:41]=2)[C@H:23]1[CH2:42][CH3:1])#[N:20]

Participants

3

Reactant 2

HCID 11096863(S,E)-3-(pent-2-enoyl)-4-phenyloxazolidin-2-oneHCID 867194294-((4S,5S)-5-(cyanomethyl)-1-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile

Product 1

HCID 867194354-((4S,5S)-5-(Cyanomethyl)-4-ethyl-1-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile

Procedure

4-((4S,5S)-5-(Cyanomethyl)-4-ethyl-1-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile was prepared from (S,E)-3-(pent-2-enoyl)-4-phenyloxazolidin-2-one following the procedure for the preparation of 4-((4S,5S)-5-(cyanomethyl)-1-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile (91G): LC-MS [M+H] 331.

Sources & evidence

ORD record
ord-37bf35e670d24378bb9184d6171145ad
Source dataset
uspto-grants-2015_09
Patent number
US09133163B2

Reaction notes

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