Ibuprofen, (+-)- → HCID 9867751, compound

HRID 1282253Notes

Reaction equation

[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)(N1C=CN=C1)=O.[OH:13][C:14]([CH:16]([C:18]1[CH:27]=[CH:26][C:21]([CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:20][CH:19]=1)[CH3:17])=[O:15].[H-].[Na+].[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH2:22]([C:21]1[CH:20]=[CH:19][C:18]([CH:16]([CH3:17])[C:14]([O:13][C:16]2[CH:17]=[CH:32][CH:31]=[C:30]([C:34]3([OH:33])[CH2:20][CH2:19][CH2:18][CH2:27][CH:11]3[CH2:12][N:8]([CH3:1])[CH3:9])[CH:14]=2)=[O:15])=[CH:27][CH:26]=1)[CH:23]([CH3:24])[CH3:25]

Participants

Reactant 4

HCID 3672Ibuprofen, (+-)-

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 9867751HCID 9867751, compound

Procedure

0.76 g (4.8 mmol) of carbonyldiimidazol were added to 1 g (4.8 mmol) of (±)-Ibuprofen in 60 ml of dry THF. The reaction was kept at room temperature for 2 h, after which a 60% solution of 0.59 g (2.4 mmol) of (RR,SS)-3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenol previously treated with 0.1 g (2.5 mmol) of sodium hydride in mineral oil was added.

Workup

additionwas added

Sources & evidence

ORD record: ord-b6586fa1da33408c98873bd1929d62a9
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455585B1

Reaction notes

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