Methanol → HCID 66958795, compound

HRID 1984417Notes

Reaction equation

HRID 1984417 reaction equation
CO.[OH-].[Li+].[C:5]([O:9][C:10]([NH:12][C:13]([CH3:29])([CH3:28])[CH2:14][C:15]1[N:19]([CH2:20][CH2:21][CH3:22])[N:18]=[C:17]([C:23]([O:25]CC)=[O:24])[CH:16]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(O)(=O)C.O>[C:5]([O:9][C:10]([NH:12][C:13]([CH3:28])([CH3:29])[CH2:14][C:15]1[N:19]([CH2:20][CH2:21][CH3:22])[N:18]=[C:17]([C:23]([OH:25])=[O:24])[CH:16]=1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66959168HCID 66959168, compound

Product 1

HCID 66958795HCID 66958795, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

Methanol (39.9 mL), lithium hydroxide (5.06 g, 121 mmol), and water (13.3 mL) were added to ethyl 5-{2-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-1-propyl-1H-pyrazole-3-carboxylate (10.65 g, 30.1 mmol) in a 500 mL round bottom flask. The mixture was stirred vigorously for 5.5 hours. Acetic acid (8.0 mL) and water (200 mL) were added. A white solid formed and more acetic acid (61 mL) was added. The solid was isolated by filtration, washed with water, and dried. A second crop of solid was isolated from the filtrate. The crops were combined to yield 8.77 g of 5-{2-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-1-propyl-1H-pyrazole-3-carboxylic acid as a white solid, mp 151-152° C. MS (APCI) m/z 326 (M+H)+; Anal. calcd for C16H27N3O4: C, 59.06; H, 8.36; N, 12.91. Found: C, 58.93; H, 8.59; N, 12.94.

Workup

  1. customA white solid formed
  2. customThe solid was isolated by filtration
  3. washwashed with water
  4. customdried
  5. customA second crop of solid was isolated from the filtrate

Sources & evidence

ORD record
ord-da99738efc794f2eadc74a442daa1e58
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

Loading…