Sodium Hydroxide → 2-(4-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid

HRID 1399651Notes

Reaction equation

HRID 1399651 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([C:12]3[C:17]([CH:18]([CH2:23][CH2:24][CH3:25])[C:19]([O:21]C)=[O:20])=[C:16]([CH3:26])[N:15]=[C:14]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:13]=3)[CH:10]=[CH:11][C:2]1=2.[OH-].[Na+]>CO>[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([C:12]3[C:17]([CH:18]([CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20])=[C:16]([CH3:26])[N:15]=[C:14]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:13]=3)[CH:10]=[CH:11][C:2]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955841Methyl 2-(4-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 669553172-(4-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acidYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 2-(4-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.092 g; 0.213 mmol), sodium hydroxide 10N (0.213 mL; 2.13 mmol) in methanol (2.1 mL). Purification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane furnished 0.063 g (70%) of the title compound as an oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane

Sources & evidence

ORD record
ord-f902caf8fb3f4bb692cb9fe7e4520232
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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