Lithium hydroxide, monohydrate → rac-5-{(2-{2-[(4-tert-Butylbenzyl)oxy]phenyl}ethyl)[2-(4-carboxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

HRID 875353Notes

Reaction equation

HRID 875353 reaction equation
[C:1]([C:5]1[CH:48]=[CH:47][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][N:19]([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]([O:45]C)=[O:44])=[CH:39][CH:38]=2)[CH:20]2[CH2:29][CH2:28][CH2:27][C:26]3[N:25]=[C:24]([C:30]([O:32]CC)=[O:31])[CH:23]=[CH:22][C:21]2=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([C:5]1[CH:48]=[CH:47][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][N:19]([CH2:35][CH2:36][C:37]2[CH:38]=[CH:39][C:40]([C:43]([OH:45])=[O:44])=[CH:41][CH:42]=2)[CH:20]2[CH2:29][CH2:28][CH2:27][C:26]3[N:25]=[C:24]([C:30]([OH:32])=[O:31])[CH:23]=[CH:22][C:21]2=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89941256rac-Ethyl 5-[(2-{2-[(4-tert-butylbenzyl)oxy]phenyl}ethyl) {2-[4-(methoxycarbonyl)phenyl]ethyl}-amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

Product 1

HCID 89941018rac-5-{(2-{2-[(4-tert-Butylbenzyl)oxy]phenyl}ethyl)[2-(4-carboxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

35 mg (0.05 mmol) of ethyl 5-[(2-{2-[(4-tert-butylbenzyl)oxy]phenyl}ethyl){2-[4-(methoxycarbo-nyl)phenyl]ethyl}amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate (Example 43A) were taken up in 1 ml of THF and 1 ml of water, and 7 mg (0.16 mmol) of lithium hydroxide monohydrate were added. The reaction was stirred at 50° C. overnight. After the reaction had gone to completion, the THF was removed on a rotary evaporator and the mixture that remained was diluted with water. The mixture was then acidified with 1 M hydrochloric acid and extracted repeatedly using a 1:1 mixture of ethyl acetate and dichloromethane. The combined organic phases were dried over magnesium sulphate, filtered and concentrated to dryness. This gave 29 mg (0.04 mmol, content 91%, 81% of theory) of the title compound as a yellowish solid.

Workup

  1. customthe THF was removed on a rotary evaporator
  2. additionthe mixture that remained was diluted with water
  3. extractionextracted repeatedly
  4. additiona 1:1 mixture of ethyl acetate and dichloromethane
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8d8f373cc8c0450b9bfabfbe846f7061
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

Loading…