Hydrochloric Acid → HCID 178445790, compound

HRID 525444Notes

Reaction equation

HRID 525444 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32]C)=[O:31])[CH2:26][CH2:25]2)=[O:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>CO>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]2)=[O:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178498434HCID 178498434, compound

Product 1

HCID 178445790HCID 178445790, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 1-(6-(trans-4-tert-butylcyclohexyloxy)-2-naphthoyl)piperidine-4-carboxylate (150 mg, 0.33 mmol) in MeOH (5 mL) was added NaOH (68 mg, 1.7 mmol, 5.0 eq) and H2O (0.5 mL). The reaction mixture was stirred at 85° C. for 2 h. After the reaction was cooled to 0° C., the pH of the solution was adjusted to 6 with 3 N HCl. The mixture was filtered and the yellow solid was the desired product 1-(6-(trans-4-tert-butylcyclohexyloxy)-2-naphthoyl)piperidine-4-carboxylic acid (90 mg, yield: 70%). ESI-MS (M+1)+: 438.3. 1HNMR (400 MHz, CD3OD) δ: 7.83˜7.81 (m, 3H), 7.41 (d, 1H), 7.28 (s, 1H), 7.16 (d, 1H), 4.44˜4.37 (m, 1H), 3.30 (br, 2H), 2.65˜2.60 (m, 1H), 2.29˜2.27 (m, 2H), 1.93˜1.90 (m, 4H), 1.44˜1.41 (m, 3H), 1.32˜1.31 (m, 2H), 1.28˜1.25 (m, 3H), 1.15˜1.12 (m, 1H), 0.92 (s, 9H). HPLC: 98.45%

Workup

  1. temperatureAfter the reaction was cooled to 0° C.
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-44d5376aa33d424588ec368c7c5fbd51
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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