Sodium Hydroxide → HCID 52914570, compound

HRID 537366Notes

Reaction equation

HRID 537366 reaction equation
[OH-].[Na+].[C:3]([C:5]1([C:44]2[CH:60]=[CH:59][CH:58]=[CH:57][C:45]=2[CH2:46][O:47][CH2:48][CH2:49][C:50]([CH3:56])([CH3:55])[C:51]([O:53]C)=[O:52])[CH2:10][CH2:9][N:8]([C:11]([C@:13]2([O:34][C:35]3[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[S:37][CH:36]=3)[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:30])[C:20]3[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=3)[C@@H:14]2[CH2:31][CH2:32][CH3:33])=[O:12])[CH2:7][CH2:6]1)#[N:4]>C1COCC1.CO>[C:3]([C:5]1([C:44]2[CH:60]=[CH:59][CH:58]=[CH:57][C:45]=2[CH2:46][O:47][CH2:48][CH2:49][C:50]([CH3:56])([CH3:55])[C:51]([OH:53])=[O:52])[CH2:10][CH2:9][N:8]([C:11]([C@:13]2([O:34][C:35]3[CH:39]=[C:38]([C:40]([F:41])([F:43])[F:42])[S:37][CH:36]=3)[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:30])[C:20]3[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=3)[C@@H:14]2[CH2:31][CH2:32][CH3:33])=[O:12])[CH2:7][CH2:6]1)#[N:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86669382HCID 86669382, compound

Product 1

HCID 52914570HCID 52914570, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2 N Aqueous sodium hydroxide (5.5 mL) was added to methyl 4-(2-(4-cyano-1-((2R,3S)-2-propyl-1-(3-(trifluoromethyl)picolinoyl)-3-(5-(trifluoromethyl)thiophen-3-yloxy)piperidine-3-carbonyl)piperidin-4-yl)benzyloxy)-2,2-dimethylbutanoate (312 mg, 0.37 mmol) in THF/methanol (1:3, 12 mL). The reaction was stirred for 8 h at room temperature then concentrated. The residue was diluted ethyl acetate (30 mL) and the pH adjusted to 1 with 1 N hydrochloric acid. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by C18 semi-prep HPLC to obtain A60 (300 mg, 99% yield) as a white powder after lyophilization from water/acetonitrile: 1H NMR (CDCl3, 300 MHz) δ 8.81-8.82 (d, J=3.9 Hz, 1H), 8.06-8.08 (d, J=8.1 Hz, 1H), 7.24-7.50 (m, 5H), 6.84-6.87 (d, J=8.1 Hz, 1H), 6.53-6.56 (m, 1H), 4.65-5.57 (m, 5H), 3.48-3.75 (m, 6H), 3.08-3.20 (m, 3H), 1.22 (s, 6H), 0.93-2.47 (m, 17H).

Workup

  1. concentrationthen concentrated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by C18 semi-prep HPLC
  7. customto obtain A60 (300 mg, 99% yield) as a white powder after lyophilization from water/acetonitrile

Sources & evidence

ORD record
ord-b50571e8b7104ae091d1406785d006ed
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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