Diethyl Ether → HCID 131713159, compound

HRID 1381382Notes

Reaction equation

HRID 1381382 reaction equation
[Cl-].[CH:2]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:59][O:60][CH3:61])[C:11]([NH:13][CH:14]2[C:57](=[O:58])[N:16]3[C:17]([C:41]([O:43][CH:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])=[C:18]([CH2:21][P+:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=[O:3].[OH-].[Na+].C(OCC)C>CC(C)=O.O>[CH:2]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:59][O:60][CH3:61])[C:11]([NH:13][CH:14]2[C:57](=[O:58])[N:16]3[C:17]([C:41]([O:43][CH:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[O:42])=[C:18]([CH:21]=[P:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 131713156HCID 131713156, compound

Product 1

HCID 131713159HCID 131713159, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

[7-{2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido}-4-benzhydryloxycarbonyl-3-cephem-3-yl]methyltriphenylphosphonium chloride (syn isomer) (5.33 g) was dissolved in a mixture of acetone (60 ml) and water (10 ml), and the solution was adjusted to pH 11 with 2N aqueous solution of sodium hydroxide, followed by extraction three times with ethyl acetate (100 ml). The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then evaporated to dryness to give a residue, which was pulverized with diethyl ether to obtain benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-triphenylphosphoranylidenemethyl-3-cephem-4-carboxylate (syn isomer) (3.7 g).

Workup

  1. extractionfollowed by extraction three times with ethyl acetate (100 ml)
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customto give a residue, which

Sources & evidence

ORD record
ord-92cf0bf834d64cfc9212ebdb5be76859
Source dataset
uspto-grants-1986_04
Patent number
US04585860

Reaction notes

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