Sodium Carbonate → HCID 13770815, compound

HRID 1681458Notes

Reaction equation

HRID 1681458 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[I-].[C:8]1([CH2:14][C:15]([NH:17][CH:18]2[C:61](=[O:62])[N:20]3[C:21]([C:45]([O:47][CH:48]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)=[O:46])=[C:22]([CH2:25][P+:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.C(Cl)Cl>[C:8]1([CH2:14][C:15]([NH:17][CH:18]2[C:61](=[O:62])[N:20]3[C:21]([C:45]([O:47][CH:48]([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)=[O:46])=[C:22]([CH:25]=[P:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 131717681HCID 131717681, compound

Product 1

HCID 13770815HCID 13770815, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

14.0 g (0.132 mol) of Na2CO3, dissolved in 150 ml of water, are added to a suspension of 78.0 g (0.088 mol) of benzhydryl 7-phenylacetamido-3-(triphenylphosphonio)methyl-3-cephem-4-carboxylate iodide (Example 7) in 400 ml of methylene chloride and the mixture is stirred vigorously at room temperature for 15 minutes. The CH2Cl2 layer is separated off, the aqueous phase is extracted again with 200 ml of CH2Cl2 and the combined organic phases are dried over sodium sulphate. The methylene chloride phase is concentrated to dryness and the residue is stirred in about 600 ml of acetone for 1 hour. The product is filtered off with suction and rinsed thoroughly with acetone.

Workup

  1. customThe CH2Cl2 layer is separated off
  2. extractionthe aqueous phase is extracted again with 200 ml of CH2Cl2
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. concentrationThe methylene chloride phase is concentrated to dryness
  5. stirringthe residue is stirred in about 600 ml of acetone for 1 hour
  6. filtrationThe product is filtered off with suction
  7. washrinsed thoroughly with acetone

Sources & evidence

ORD record
ord-ee65378d140f4f29b1cb4f17ea900d1a
Source dataset
uspto-grants-1992_12
Patent number
US05171854

Reaction notes

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