Sodium Azide → HCID 68147541, compound

HRID 1076698Notes

Reaction equation

HRID 1076698 reaction equation
[N-]=[N+]=[N-].[Na+].[C:5]1([C:11]([NH:24][CH:25]2[C:47](=[O:48])[N:27]3[CH:28]([C:33]4[N:37]([CH2:38][C:39]5[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=5)[N:36]=[N:35][N:34]=4)[C:29]([CH3:32])([CH3:31])[S:30][C@H:26]23)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[C:5]1([C:11]([NH:24][CH:25]2[C:47](=[O:48])[N:27]3[CH:28]([C:33]4[N:37]([CH2:38][C:39]5[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=5)[N:36]=[N:35][N:34]=4)[C:29]([C:31]4[CH:19]=[CH:18][CH:11]=[CH:12][CH:13]=4)([C:32]4[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=4)[S:30][C@H:26]23)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 70605636HCID 70605636, compound

Product 1

HCID 68147541HCID 68147541, compound

Procedure

To the solution of 6-(triphenylmethylamino)-2,2-dimethyl-3-(p-tolylsulfonyloxy-[N-(p-methoxybenzylimino]methyl)penam prepared above is added 1.63 g. (1.25 equivalents) of sodium azide and the mixture allowed to stir at room temperature for 24 hours. The mixture is quenched in 3 l. of ice water and the biphasic system allowed to stir for 15 min. The resulting oily solid is filtered, trituated with water and subsequently recrystallized from chloroformisopropanol, 3.38 g., m.p. 177°-180° C. Further recrystallization raises the melting point to 186°-188° C., and provides a product which is essentially one spot in a benzene(200):ethyl acetate(10) silica gel chromatography system and indistinguishable from the final product of Example 1.

Workup

  1. additionabove is added 1.63 g
  2. customThe mixture is quenched in 3 l
  3. stirringto stir for 15 min
  4. filtrationThe resulting oily solid is filtered
  5. customsubsequently recrystallized from chloroformisopropanol, 3.38 g
  6. customFurther recrystallization
  7. temperatureraises the melting point to 186°-188° C.
  8. customprovides a product which

Sources & evidence

ORD record
ord-b926626f5f3843a7ba4d569a47c7bed1
Source dataset
uspto-grants-1976_05
Patent number
US03957811

Reaction notes

Loading…