Ammonium Chloride → HCID 59128868, compound

HRID 2390504Notes

Reaction equation

HRID 2390504 reaction equation
[C:1]([C:5]1[CH:32]=[CH:31][CH:30]=[CH:29][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:19][C:18]([C:20]([CH3:28])([CH3:27])[CH2:21][CH2:22][C:23]([O:25]C)=[O:24])=[N:17][N:16]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].[Cl-].[NH4+]>C1COCC1.O>[C:1]([C:5]1[CH:32]=[CH:31][CH:30]=[CH:29][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:19][C:18]([C:20]([CH3:27])([CH3:28])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[N:17][N:16]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 59128957HCID 59128957, compound

Product 1

HCID 59128868HCID 59128868, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(5-(2-(2-tert-butylphenoxy)pyridin-3-ylamino)-1,3,4-thiadiazol-2-yl)-4-methylpentanoate (Example 96) (450 mg, 1.0 mmol), lithium hydroxide hydrate (125 mg, 3 mmol) in THF (10 mL) and water (2 mL) was stirred at rt for 2 h. A solution of saturated ammonium chloride was added and mixture was extracted twice using ethyl acetate. The organic phase was separated, dried (MgSO4), filtered and evaporated. The crude material was purified by preparative HPLC to give the title compound (430 mg, TFA salt) as a white solid. (M+H)+=441.

Workup

  1. extractionmixture was extracted twice using ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-84a69d2a2416437d9a9e4c00ff2b0eb3
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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