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Hydrochloric Acid → (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

HRID 472855
Notes
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Reaction equation

HRID 472855 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:30])=[N:13][C:14]2[N:15]([N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH:22]=2)[C:16]=1[CH:17]([CH3:19])[CH3:18])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:30])=[N:13][C:14]2[N:15]([N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH:22]=2)[C:16]=1[CH:17]([CH3:19])[CH3:18])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66691616(S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 66693671(S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A solution of (S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.060 g, 0.140 mmol) and 1M NaOH (1 ml, 1.000 mmol) in MeOH (5 mL) was heated at 60° C. for 16 h. Then, the reaction mixture was cooled, neutralized with 1M HCl (1 mL), concentrated and the residue was diluted with Et2O (25 mL), washed with 0.1M NH4OAc (5 mL), brine (5 mL), dried (Na2SO4), filtered and concentrated to give (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isopropyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (0.055 g, 0.131 mmol, 94% yield) as white solid and 98% ee. 1H NMR (500 MHz, CDCl3) δ: 7.96 (s, 1H), 7.83 (d, J=7.0 Hz, 1H), 7.39-7.30 (m, 2H), 6.81 (s, 1H), 5.46 (br. s., 1H), 3.99 (br. s., 1H), 2.74 (br. s., 3H), 1.69 (d, J=6.4 Hz, 3H), 1.57 (br. s., 3H), 1.27 (s, 9H). LCMS (M+H) calcd for C22H27ClN3O3: 416.17. found: 416.3.

Workup

  1. temperatureThen, the reaction mixture was cooled
  2. concentrationconcentrated
  3. additionthe residue was diluted with Et2O (25 mL)
  4. washwashed with 0.1M NH4OAc (5 mL), brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4847fdd8abb8492ba73df2ec7d833413
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633200B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes