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Hydrochloric Acid → 5-(Benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid

HRID 1626782
Notes
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Reaction equation

HRID 1626782 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:37]([O:39]C(C)(C)C)=[O:38])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][OH:36])=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1.CO>[CH2:1]([O:8][C:9]1[C:10]([C:37]([OH:39])=[O:38])=[N:11][C:12]([CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][OH:36])=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)[CH2:21][CH2:22]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68193244tert-Butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

Product 1

HCID 681931825-(Benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 5-(benzyloxy)-2-{(1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate (0.81 g, 1.4 mmol) was dissolved in a mixed solvent of tetrahydrofuran (10 mL) and methanol (10 mL), and an aqueous sodium hydroxide solution (5 M, 10 mL, 50 mmol) was added, followed by stirring at 50° C. for 15 minutes. The reaction solution was cooled to room temperature, and hydrochloric acid (5 M, 10 mL, 50 mmol) was added, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure to afford 5-(benzyloxy)-2-{(1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylic acid as a yellow solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-890f037ccef44c108a08c8f376a5b915
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785462B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes