Hydrochloric Acid → HCID 66673118, compound

HRID 423540Notes

Reaction equation

HRID 423540 reaction equation
[CH3:1][CH:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]2[CH:16]=[N:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[OH-].[Na+].Cl>C(O)C>[CH3:3][CH:2]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=3)=[N:17][CH:16]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66673173HCID 66673173, compound

Product 1

HCID 66673118HCID 66673118, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methylethyl-4-{[(6-{4-[(ethyloxy)carbonyl]phenyl}-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.3 g, 0.70 mmol) was added to a solution of NaOH (0.06 g, 1.4 mmol) in ethanol (10 mL). The reaction mixture was stirred overnight, neutralized with 1N HCl and freeze-dried to give 4-(5-{[(1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinyl)methyl]oxy}-2-pyridinyl)benzoic acid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (d, 1H, J=3.0 Hz), 8.12 (d, 2H, J=8.7 Hz), 8.01-7.97 (m, 3H), 7.53-7.49 (m, 1H), 4.77-4.71 (m, 1H), 4.04-3.94 (m, 4H), 2.07 (bs, 3H), 1.80-1.72 (m, 2H), 1.19-1.13 (m, 8H); LRMS (ESI), m/z 399 (M+H).

Workup

  1. customfreeze-dried

Sources & evidence

ORD record
ord-99d5e5df0fba40b2b00a4f94681db217
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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