Hydrochloric Acid → HCID 118307869, compound

HRID 718471Notes

Reaction equation

HRID 718471 reaction equation
[OH-].[K+].[C:3]([O:7][C@@H:8]([C:15]1[C:16]([CH3:47])=[N:17][C:18]([CH3:46])=[C:19]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[CH:32][CH:31]=2)[C:20]=1[N:21]1[CH2:26][CH2:25][C:24](=[C:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]1)[C:9]([O:11]C(C)C)=[O:10])([CH3:6])([CH3:5])[CH3:4].Cl>C(O)C>[C:3]([O:7][C@@H:8]([C:15]1[C:16]([CH3:47])=[N:17][C:18]([CH3:46])=[C:19]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[CH:34][CH:35]=2)[C:20]=1[N:21]1[CH2:26][CH2:25][C:24](=[C:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]1)[C:9]([OH:11])=[O:10])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 118307790HCID 118307790, compound

Product 1

HCID 118307869HCID 118307869, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

The potassium hydroxide (54.6 mg, 0.97 mmol) was added to a station (S)-isopropyl 2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-2,6-dimethyl-4-(4-(propan-2-ylidene)piperidin-1-yl)pyridin-3-yl)acetate (60 mg, 0.097 mmol) in ethanol (2 mL) and stirred for 6 h at 90° C. The reaction mixture was neutralized with 1N HCl solution, extracted with EtOAc, and the organic layer was washed with brine, and dried (MgSO4). The crude material was purified by prep HPLC to afford (S)-2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-2,6-dimethyl-4-(4-(propan-2-ylidene)piperidin-1-yl)pyridin-3-yl)acetic acid 39.3 mg (70%). 1H NMR (500 MHz, DMSO-d6) δ 7.38-7.35 (m, 2H), 7.19 (d, J=8.4 Hz, 1H), 7.13 (t, J=8.4 Hz, 2H), 6.97 (t, J=8.1 Hz, 2H), 6.90 (d, J=8.1 Hz, 1H), 5.84 (s, 1H), 4.21 (t, J=6.2 Hz, 2H), 3.53 (br. s, 4H), 3.04 (t, J=6.2 Hz, 2H), 2.44 (s, 3H), 2.31-2.28 (m, 1H), 2.05 (br. s, 1H), 2.00 (s, 3H), 1.83 (br. s, 1H), 1.65 (br. s, 1H), 1.56 (s, 3H), 1.49 (s, 3H), 1.12 (s, 9H). UPLC (M+H)=575.3.

Workup

  1. extractionextracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-00fa007939914a0daaa9ad1081a662d6
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

Loading…