Hydrochloric Acid → (4-{2-[(1S,2R)-2-(1-{[(1-methylcyclopropyl)oxy]carbonyl}piperidin-4-yl)cyclopropyl]ethoxy}phenyl)acetic acid

HRID 1850759Notes

Reaction equation

HRID 1850759 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:29]=[CH:28][C:8]([O:9][CH2:10][CH2:11][C@@H:12]2[CH2:14][C@@H:13]2[CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]3([CH3:27])[CH2:26][CH2:25]3)=[O:22])[CH2:17][CH2:16]2)=[CH:7][CH:6]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH3:27][C:24]1([O:23][C:21]([N:18]2[CH2:19][CH2:20][CH:15]([C@H:13]3[CH2:14][C@H:12]3[CH2:11][CH2:10][O:9][C:8]3[CH:28]=[CH:29][C:5]([CH2:4][C:3]([OH:30])=[O:2])=[CH:6][CH:7]=3)[CH2:16][CH2:17]2)=[O:22])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 708560031-methylcyclopropyl 4-((1R,2S)-2-{2-[4-(2-methoxy-2-oxoethyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carboxylate

Product 1

HCID 70856316(4-{2-[(1S,2R)-2-(1-{[(1-methylcyclopropyl)oxy]carbonyl}piperidin-4-yl)cyclopropyl]ethoxy}phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 1-methylcyclopropyl 4-((1R,2S)-2-{2-[4-(2-methoxy-2-oxoethyl)phenoxy]ethyl}cyclopropyl)piperidine-1-carboxylate (Example 53, Step A, 88 mg, 0.21 mmol) in a 1:1:1 mixture of THF/methanol/water (3 mL) was added lithium hydroxide (10.7 mg, 0.44 mmol) and the resulting mixture stirred for 2 h at RT. The mixture was neutralized via addition of 1N aqueous HCl until pH of 7 was obtained. The solution was then extracted with ethyl acetate (3×10 mL). The organics were combined, dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford the title compound used for the next reaction without further purification. HPLC/MS; 1.22 min, 401 (M+H)+.

Workup

  1. customwas obtained
  2. extractionThe solution was then extracted with ethyl acetate (3×10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-25febf6fd4b0471c97cd081c1dcee30b
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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