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Hydrochloric Acid → 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

HRID 20567
Notes
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Reaction equation

HRID 20567 reaction equation
[Si]([O:8][CH2:9][C@H:10]([CH3:39])[O:11][C:12]1[CH:13]=[C:14]([CH:27]=[C:28]([C:30]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH3:38])[N:34]=2)=[O:31])[CH:29]=1)[O:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=1)(C(C)(C)C)(C)C.O.[OH-].[Li+].Cl>C1COCC1.O>[OH:8][CH2:9][C@H:10]([CH3:39])[O:11][C:12]1[CH:13]=[C:14]([CH:27]=[C:28]([C:30]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH3:38])[N:34]=2)=[O:31])[CH:29]=1)[O:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59346889ethyl 4-(3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate

Product 1

HCID 593468664-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acidYield 108.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-(3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate (3.78 g, 6.84 mmol) in THF (100 mL) was added to a solution of lithium hydroxide monohydrate (1.44 g, 33 mmol) in water (50 mL). The mixture was stirred at ambient temperature for 72 hours. 1M Hydrochloric acid was added until pH=2 and the mixture stirred for a further 1 hour. The THF was removed in vacuo and the solid precipitate filtered off, washed with water and dried in vacuo to give the desired compound (3.06 g).

Workup

  1. stirringthe mixture stirred for a further 1 hour
  2. customThe THF was removed in vacuo
  3. filtrationthe solid precipitate filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b7b6a3497844411496c26ab826c0a325
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745475B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes