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Hydrochloric Acid → HCID 11433023, compound

HRID 732230
Notes
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Reaction equation

HRID 732230 reaction equation
[F:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:25]3[S:26][CH:27]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:29]=3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:3]([O:5]CC)=[O:4].O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[F:1][CH:2]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:25]3[S:26][CH:27]=[C:28]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:29]=3)=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)[C:3]([OH:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23143237HCID 23143237, compound

Product 1

HCID 11433023HCID 11433023, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-fluoro-3-{4-[(4-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}-propanoate (740 mg, 1.31 mmol), tetrahydrofuran (15 mL), methanol (10 mL), water (10 mL) and lithium hydroxide monohydrate (165 mg, 3.92 mmol) was stirred at room temperature for 3 hr. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from hexane-diisopropyl ether to give the title compound (505 mg, yield 68%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from hexane-diisopropyl ether

Sources & evidence

ORD record
ord-8dd78c1699cc4c39b1fe95fae90979ca
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07585880B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes