Triethylamine → HCID 178451424, compound

HRID 275571Notes

Reaction equation

HRID 275571 reaction equation
[C:1]([O:5]C(ON=C(C1C=CC=CC=1)C#N)=O)([CH3:4])([CH3:3])[CH3:2].[PH:19](=[O:22])([OH:21])[OH:20].C(C(C(C)C)C1NC1[C:29]1[N:33]=[CH:32][N:31]([C:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:30]=1)(C)C.[CH2:57]([N:59]([CH2:62]C)[CH2:60][CH3:61])C>O1CCOCC1.O.O>[PH:19](=[O:20])([OH:22])[OH:21].[C:1]([O:5][C:62]([N:59]1[CH:60]([CH2:61][C:29]2[N:33]=[CH:32][N:31]([C:34]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:30]=2)[CH2:57]1)=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 178442548HCID 178442548, compound

Product 1

HCID 178451424HCID 178451424, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON, 2.82 g) was added portionwise to a stirred solution of diisopropyl (2RS,3RS)-2,3-epimino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (2.76 g, prepared as described in Example 58) and triethylamine (2.17 ml) in dioxan-water (2:1, 75 ml). The mixture was stirred at room temperature for seven hours, allowed to stand for a further three days, diluted with water (50 ml) and extracted with chloroform (3×50 ml). The organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified using HPLC on silica, with ethyl acetate as eluant, to give diisopropyl (2RS,3RS)-2,3(N-tert-butoxycarbonylepimino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.22 g, m.p. 30°-31° C.). NMR (CDCl3): δ 1.25(12H,m), 1.33(9H,s), 1.70(1H,m), 2.23(1H,m), 3.35(1H,m), 3.53(1H,d), 4.68(2H,m), 7.1-7.4(15H,m), 7.85(1H,s). IR: 1724 cm-1.

Workup

  1. waitto stand for a further three days
  2. extractionextracted with chloroform (3×50 ml)
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-f219dfbd222545ed82bc40fb24cf872d
Source dataset
uspto-grants-1995_02
Patent number
US05393732

Reaction notes

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