Diethyl Ether → HCID 54340141, compound

HRID 434729Notes

Reaction equation

HRID 434729 reaction equation
C(N(CC)CC)C.[CH:8]([O:21][C:22]([C:24]1[N:25]2[CH:28]([O:29][CH2:30][C:31]=1[CH2:32][CH:33]=[O:34])[CH:27]([NH:35][C:36](=[O:66])[C:37](=[N:63][O:64][CH3:65])[C:38]1[N:39]=[C:40]([NH:43][C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[S:41][CH:42]=1)[C:26]2=[O:67])=[O:23])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[S:68](Cl)([C:71]1[CH:77]=[CH:76][C:74]([CH3:75])=[CH:73][CH:72]=1)(=[O:70])=[O:69].CCOCC>C(Cl)Cl>[CH:8]([O:21][C:22]([C:24]1[N:25]2[CH:28]([O:29][CH2:30][C:31]=1[CH:32]=[CH:33][O:34][S:68]([C:71]1[CH:77]=[CH:76][C:74]([CH3:75])=[CH:73][CH:72]=1)(=[O:70])=[O:69])[CH:27]([NH:35][C:36](=[O:66])[C:37](=[N:63][O:64][CH3:65])[C:38]1[N:39]=[C:40]([NH:43][C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[S:41][CH:42]=1)[C:26]2=[O:67])=[O:23])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 54206503HCID 54206503, compound

Product 1

HCID 54340141HCID 54340141, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Triethylamine (0.27 cc) is added, in the course of 10 minutes, to a solution, cooled to -5° C., of the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-(2-oxoethyl)-5-oxa-1-azabicyclo-[4.2.0]oct-2-ene (1.00 g) and tosyl chloride (0.35 g) in methylene chloride (20 cc). The mixture is stirred at -5° C. for 10 minutes and then left to return to 20° C. The mixture is then stirred for 30 minutes. The solvent is evaporated off under reduced pressure (350 mm Hg; 47 kPa). This yields a chestnut-coloured oil, which solidifies on stirring with ether (100 cc). The solid is filtered off and dried. This yields the E form of the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-8-oxo-3-(2-tosyloxyvinyl)-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (0.38 g) in the form of a cream-coloured powder. The filtrate is concentrated to a residual volume of 5 cc and isopropyl ether (100 cc) is added. A pale yellow solid separates out. It is isolated on a filter and a second fraction of the E form of the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-(2-tosyloxyvinyl)-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (0.11 g) is obtained.

Workup

  1. waitleft
  2. customto return to 20° C
  3. stirringThe mixture is then stirred for 30 minutes
  4. customThe solvent is evaporated off under reduced pressure (350 mm Hg; 47 kPa)
  5. customThis yields a chestnut-coloured oil, which
  6. filtrationThe solid is filtered off
  7. customdried

Sources & evidence

ORD record
ord-41c58a5cbd0846bcbf9d72fd0e379fb9
Source dataset
uspto-grants-1983_08
Patent number
US04399135

Reaction notes

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