Ammonium Chloride → HCID 131718903, compound

HRID 275570Notes

Reaction equation

HRID 275570 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].C([CH:8](C(C)C)[CH:9]1[NH: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)(C)C.[N-:39]=[N+:40]=[N-:41].[Na+].[Cl-].[NH4+]>CO.O>[NH2:35][CH:9]([CH:10]([N:39]=[N+:40]=[N-:41])[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:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:12]=1)[CH2:8][P:1]([O:3][CH:16]([CH3:23])[CH3:17])(=[O:2])[O:4][CH:9]([CH3:10])[CH3:8]

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 178442548HCID 178442548, compound

Product 1

HCID 131718903HCID 131718903, compoundYield 162.1%

Reagents, catalysts & solvents 1

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

Procedure

A stirred mixture of diisopropyl(2RS,3RS)-2,3-epimino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (2.6 g, prepared as described in Example 58), sodium azide (1.59 g), ammonium chloride (0.58 g) and methanol-water (8:1, 50 ml) was heated under reflux for six hours, then allowed to stand at room temperture for three days. Further quantities of sodium azide (0.80 g) and ammonium chloride (0.29 g) were added and the mixture heated for a further six hours. It was then filtered through silica, using chloroform as eluant, dried, evaporated and chromatographed on silica, using chloroform-hexane-methanol (15:3:1) as eluant, to give diisopropyl(2RS,3SR)-2-amino-3-azido-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (2.27 g) as a yellow oil. NMR (CDCl3): δ1.3(12H,m), 1.65-1.85(1H,m), 2.12-2.28(1H,m), 3.65(1H,m), 4.58(1H,d), 4.68(2H,m), 7.05-7.38(15H,m), 8.00(1H,s). Regiochemistry was confirmed by extensive NMR studies on acetylated material.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for six hours
  3. temperaturethe mixture heated for a further six hours
  4. filtrationIt was then filtered through silica
  5. customdried
  6. customevaporated
  7. customchromatographed on silica

Sources & evidence

ORD record
ord-72c736e755304f89a2a5a71dec1e06a5
Source dataset
uspto-grants-1995_02
Patent number
US05393732

Reaction notes

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