Sodium Hydroxide → 2-(3-(1-(Tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 2045617Notes

Reaction equation

HRID 2045617 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]([C:15]2[CH:16]=[C:17]([CH:21]3[C:30]([CH3:32])([CH3:31])[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:33]([O:35]C)=[O:34])[CH:27]=4)[NH:22]3)[CH:18]=[CH:19][CH:20]=2)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:12][C:13]([C:15]2[CH:16]=[C:17]([CH:21]3[C:30]([CH3:32])([CH3:31])[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:33]([OH:35])=[O:34])[CH:27]=4)[NH:22]3)[CH:18]=[CH:19][CH:20]=2)=[O:14])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441328Methyl 2-(3-(1-(tert-butoxycarbonyl) azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 534923202-(3-(1-(Tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(1-(tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (234 mg, 0.44 mmol of theory) in methanol (6.8 mL) and 1 M sodium hydroxide aqueous solution (5.3 mL, 5.3 mmol, 12.0 eq.) was heated to reflux for 60 min, LC-MS showed the reaction was complete and only the desired product formed. The solvent was concentrate in vacuo and the residue was dissolved in water and acidified with 1 M hydrochloric acid solution to pH=6. The white precipitated solid was extracted with tetrahydrofuran (twice). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate. Removal of the solvent gave 209 mg product as a white solid, which was purified by column chromatography (Pure ethyl acetate) to afford 78 mg of 2-(3-(1-(tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 37.2%. MS (ESI+APCI) M+1=480.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 60 min

Sources & evidence

ORD record
ord-1fc2c7aca0514e8f97161c841d00f5f5
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

Loading…