Sodium Hydroxide → HCID 87272897, compound

HRID 537358Notes

Reaction equation

HRID 537358 reaction equation
[C:1]1([C:7]2([CH2:46][CH2:47][CH2:48][CH2:49][C:50]([O:52]CC)=[O:51])[CH2:12][CH2:11][N:10]([C:13]([C@:15]3([O:36][C:37]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[S:39][CH:38]=4)[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:32])[C:22]4[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=4)[C@@H:16]3[CH2:33][CH2:34][CH3:35])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:7]2([CH2:46][CH2:47][CH2:48][CH2:49][C:50]([OH:52])=[O:51])[CH2:8][CH2:9][N:10]([C:13]([C@:15]3([O:36][C:37]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[S:39][CH:38]=4)[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:32])[C:22]4[C:27]([C:28]([F:30])([F:29])[F:31])=[CH:26][CH:25]=[CH:24][N:23]=4)[C@@H:16]3[CH2:33][CH2:34][CH3:35])=[O:14])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87273341HCID 87273341, compound

Product 1

HCID 87272897HCID 87272897, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To ethyl 5-(4-phenyl-1-((2R,3S)-2-propyl-1-(3-(trifluoromethyl)picolinoyl)-3-(5-(trifluoromethyl)thiophen-3-yloxy)piperidine-3-carbonyl)piperidin-4-yl)pentanoate in ethanol was added 2.0 M NaOH aqueous solution and the mixture was stirred at 70° C. for 1 h. Then the solvent was removed in vacuo. The residue was redissolved in water, acidified with 6N HCl to PH ˜4, then extracted with EtOAc (2×30 ml), dried (MgSO4), concentrated, purified on Gilson, treated with 4.0 M HCl in dioxane (2-3 drops), lyophilized, to give 5-(4-phenyl-1-((2R,3S)-2-propyl-1-(3-(trifluoromethyl)picolinoyl)-3-(5-(trifluoromethyl)thiophen-3-yloxy)piperidine-3-carbonyl)piperidin-4-yl)pentanoic acid A81 as white solid.

Workup

  1. customThen the solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in water
  3. extractionextracted with EtOAc (2×30 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified on Gilson
  7. additiontreated with 4.0 M HCl in dioxane (2-3 drops)

Sources & evidence

ORD record
ord-ef0a239e0c4d483f883ee6ae68c336cb
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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