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Hydrochloric Acid → (R)-(4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)-hydroxy-acetic Acid

HRID 547102
Notes
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Reaction equation

HRID 547102 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:41])[C@@H:6]([C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:38][CH3:39])([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]([OH:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[C:25]([CH3:37])[CH:24]=3)[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:40])[CH:11]=[CH:12][CH:13]=1)[OH:7].Cl>CO>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C@@H:6]([OH:7])[C:5]([OH:41])=[O:4])[CH:9]=2)=[C:15]([CH3:40])[CH:16]=1)([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]([OH:36])[C:32]([CH3:34])([CH3:35])[CH3:33])=[C:25]([CH3:37])[CH:24]=1)[CH2:38][CH3:39])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57708910(R)-(4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)hydroxy-acetic acid methyl ester

Product 1

HCID 57709134(R)-(4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)-hydroxy-acetic AcidYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 N sodium hydroxide aqueous solution (0.010 mL) was added to a solution of (R)-(4′-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2′-methyl-biphenyl-3-yl)hydroxy-acetic acid methyl ester (Example 156-(3); 2.6 mg, 0.0048 mmol) in methanol (0.10 mL) at room temperature, and the mixture was stirred at room temperature for four hours. The mixture was acidified with dilute hydrochloric acid aqueous solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give the title compound (2.5 mg, 100%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c79817c4da344eb7af5bc879e6526371
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes