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

HRID 472859Notes

Reaction equation

HRID 472859 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:31])=[N:13][C:14]2[N:15]([N:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH:23]=2)[C:16]=1[CH2:17][CH:18]([CH3:20])[CH3:19])[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]([CH3:31])=[N:13][C:14]2[N:15]([N:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH:23]=2)[C:16]=1[CH2:17][CH:18]([CH3:20])[CH3:19])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66693018(S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isobutyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 66693750(S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isobutyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isobutyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.035 g, 0.079 mmol) and 1M NaOH (0.788 ml, 0.788 mmol) in MeOH (5 mL) was heated at reflux for 4 h. Then, cooled, neutralized with 1M HCl (0.8 mL), concentrated and the residue was taken up in Et2O (25 mL), washed with water (5 mL), brine (5 mL), dried (MgSO4), filtered and concentrated to give (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-isobutyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (0.0303 g, 0.069 mmol, 88% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ: 7.99-7.96 (m, 1H), 7.85 (dt, J=7.3, 1.4 Hz, 1H), 7.41-7.33 (m, 2H), 6.82 (s, 1H), 5.41 (s, 1H), 3.75-3.56 (m, 1H), 3.05-2.92 (m, 1H), 2.65 (s, 3H), 2.55 (br. s., 1H), 1.29 (s, 9H), 1.09 (d, J=6.7 Hz, 3H), 1.02 (d, J=6.4 Hz, 3H). LCMS (M+H) calcd for C23H29ClN3O3: 430.19. found: 430.3.

Workup

  1. temperatureat reflux for 4 h
  2. temperatureThen, cooled
  3. concentrationconcentrated
  4. washwashed with water (5 mL), brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-21636b170b3b42a2b273d45979c2f841
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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