Ammonium Chloride → HCID 68833152, compound

HRID 1454104Notes

Reaction equation

HRID 1454104 reaction equation
C([N:4](C(C)C)CC)(C)C.[CH2:10]([O:17][C:18](=[O:38])[CH:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][Si](C(C)(C)C)(C)C)=[CH:26][CH:25]=1)[CH2:20][C:21](O)=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[NH2:4][C:21](=[O:22])[CH2:20][CH:19]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:38]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68833938HCID 68833938, compound

Product 1

HCID 68833152HCID 68833152, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Di-iso-propylethylamine (1.03 g, 1.40 mL, 8.00 mmol) was added in one portion to a stirred suspension of 4-(benzyloxy)-3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-oxobutanoic acid (0.83 g, 2.0 mmol), ammonium chloride (0.107 g, 2.00 mmol) and N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (837 mg, 2.20 mmol) in dimethylformamide (15 mL) at room temperature under nitrogen. After stirring for 2 h the volatiles were evaporated and the residue partitioned between dichloromethane (50 mL) and aqueous hydrochloric acid solution (1.0 M; 50 mL). The resulting bi-phasic mixture was stirred at room temperature for 30 min after which the phases were separated and the aqueous layer washed with dichloromethane (2×50 mL). The organic layers were combined, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (10% methanol: dichloromethane) to give the title compound as a white solid (0.45 g, 60%). LC/MS: 2.55 min; z/e 300, calcd (M+1) 300. 1H NMR (400 MHz: CDCl3): 7.25 (3H), 7.15 (2H), 7.10 (2H), 6.75 (2H), 6.35 (1H), 6.65 (1H), 5.45 (1H), 5.10 (2H), 4.10 (1H), 3.05 (1H), 2.55 (1H).

Workup

  1. customwere evaporated
  2. customthe residue partitioned between dichloromethane (50 mL) and aqueous hydrochloric acid solution (1.0 M; 50 mL)
  3. stirringThe resulting bi-phasic mixture was stirred at room temperature for 30 min after which the phases
  4. customwere separated
  5. washthe aqueous layer washed with dichloromethane (2×50 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silica gel (10% methanol: dichloromethane)

Sources & evidence

ORD record
ord-1517b5caa4ed4005bf82bc370bab0ae9
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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