Sodium Hydroxide → HCID 73058303, compound

HRID 875358Notes

Reaction equation

HRID 875358 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]([F:56])([F:55])[F:54])=[CH:49][CH:48]=3)=[CH:41][CH:40]=2)[CH:14]2[CH2:23][CH2:22][CH2:21][C:20]3[N:19]=[C:18]([C:24]([O:26]CC)=[O:25])[CH:17]=[CH:16][C:15]2=3)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>O1CCOCC1>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([CH2:45][CH2:46][C:47]3[CH:48]=[CH:49][C:50]([C:53]([F:55])([F:54])[F:56])=[CH:51][CH:52]=3)=[CH:43][CH:44]=2)[CH:14]2[CH2:23][CH2:22][CH2:21][C:20]3[N:19]=[C:18]([C:24]([OH:26])=[O:25])[CH:17]=[CH:16][C:15]2=3)=[CH:7][CH:6]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86709838Ethyl 5-[{2-[4-(methoxycarbonyl)phenyl]ethyl}(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}-benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

Product 1

HCID 73058303HCID 73058303, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

98 mg (0.13 mmol) of ethyl 5-[{2-[4-(methoxycarbonyl)phenyl]ethyl}(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 2, Example 156A) were dissolved in 2.5 ml of dioxane, 0.4 ml of 1 N aqueous sodium hydroxide solution was added and the mixture was then stirred at room temperature overnight. After the reaction had gone to completion, the dioxane was removed on a rotary evaporator and the mixture that remained was diluted with water. The mixture was then acidified with acetic acid to pH 4-5. The precipitated solid was filtered off with suction, washed repeatedly with water and then dried in a drying cabinet under reduced pressure at 40° C. for three days. This gave 71 mg (73% of theory) of the title compound.

Workup

  1. customthe dioxane was removed on a rotary evaporator
  2. additionthe mixture that remained was diluted with water
  3. filtrationThe precipitated solid was filtered off with suction
  4. washwashed repeatedly with water
  5. customdried in a drying cabinet under reduced pressure at 40° C. for three days

Sources & evidence

ORD record
ord-c078e124928a4ba6ae14aaf433637549
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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