Sodium Hydroxide → HCID 59865659, compound

HRID 536711Notes

Reaction equation

HRID 536711 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)/[C:7](=[N:15]/C(=O)C(F)(F)F)/[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14]2)[C:7](=[NH:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178480296HCID 178480296, compound

Product 1

HCID 59865659HCID 59865659, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 27E (6.37 g, 21 mmol) and 6N NaOH aqueous (20 mL) in MeOH (100 mL) was stirred at 50° C. overnight, and then concentrated under reduced pressure. The residue was extracted by CH2Cl2 (30 mL×3) and the combined organic layers were washed with brine and concentrated to yield 3.8 g (87%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.37-0.44 (m, 2H), 0.47-0.54 (m, 2H), 1.07-1.20 (m, 1H), 1.29-1.36 (m, 9H), 3.78 (s, 3H), 4.10 (d, J=6.74 Hz, 2H), 5.60 (s, 1H), 7.19 (s, 1H); MS (+DCI) m/z 208 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue was extracted by CH2Cl2 (30 mL×3)
  3. washthe combined organic layers were washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-939e2c58d55044fcafeddea6ceb48c81
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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