Ammonium Chloride → HCID 178443787, compound

HRID 582187Notes

Reaction equation

HRID 582187 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].[CH:5]([CH:8]([CH:36]([CH3:38])[CH3:37])[CH:9]1[O:35][CH:10]1[C:11]1[N:15]=[CH:14][N:13]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1)([CH3:7])[CH3:6].[N-:39]=[N+:40]=[N-:41].[Na+].[Cl-].[NH4+]>CO.O>[PH:1](=[O:2])([OH:4])[OH:3].[CH:5]([CH:8]([CH:36]([CH3:38])[CH3:37])[CH:9]([OH:35])[CH:10]([N:39]=[N+:40]=[N-:41])[C:11]1[N:15]=[CH:14][N:13]([C:16]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:12]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 178442557HCID 178442557, compound

Product 1

HCID 178443787HCID 178443787, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of diisopropyl (2RS,3SR)-2,3-epoxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (6.83 g prepared as described in Example 51), sodium azide (4.18 g), ammonium chloride (1.51 g) and methanol-water (8:1, 125 ml) was heated under reflux for six hours, then concentrated under reduced pressure. The residue was filtered through silica in chloroform, then chromatographed on silica, using ethyl acetate-ethanol (20:1) as eluant, to give diisopropyl (2RS,3RS)-3-azido-2-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (5.22 g, m.p. 137-139° C., after trituration with ether). IR (nujol): 3304, 2104 cm-1. NMR (CDCl3 : δ 1.3(12H,m), 1.9-2.25(2H,m), 4.17(1H,d), 4.45(1H,m), 4.68(2H,m), 4.78(1H,d), 7.1-7.4(15H,m), 7.98(1H,s). 13C NMR confirmed the regiochemistry.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for six hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe residue was filtered through silica in chloroform
  5. customchromatographed on silica

Sources & evidence

ORD record
ord-e8a565d1126b48b0973de2138a92c020
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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