Tetrahydrofuran → HCID 131710675, compound

HRID 596840Notes

Reaction equation

HRID 596840 reaction equation
[NH2:1][CH:2]1[C:28](=[O:29])[N:4]2[C:5]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:6]([C:9](=[O:11])[CH3:10])[CH2:7][S:8][C@H:3]12.O1CCCC1.C(=O)(O)[O-].[Na+].[CH:40]([O:42][CH:43]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:44](Cl)=[O:45])=[O:41]>C(OCC)(=O)C>[CH:40]([O:42][CH:43]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:44]([NH:1][CH:2]1[C:28](=[O:29])[N:4]2[C:5]([C:12]([O:14][CH:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:6]([C:9](=[O:11])[CH3:10])[CH2:7][S:8][C@H:3]12)=[O:45])=[O:41]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11986429169-64-0HCID 516892Sodium BicarbonateHCID 131710674HCID 131710674, compound

Product 1

HCID 131710675HCID 131710675, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.), stirred solution of 0.270 g. of benzhydryl 7-amino-3-acetyl-3-cephem-4-carboxylate in 20 ml. of dry tetrahydrofuran was added 0.0612 g. of sodium bicarbonate and dropwise, a solution of 0.144 g. of 2-formyloxy-2-phenylacetyl chloride in 2 ml. of tetrahydrofuran. The reaction mixture was allowed to stir with cooling for 30 minutes after which time it was transferred to a separatory funnel with the aid of cold ethyl acetate and washed with water, and brine (2X) and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided a residue which was chromatographed on silica gel using a toluene-ethyl acetate gradient to give 0.194 g. (51.2 percent) of the title product as a white froth:

Workup

  1. stirringto stir
  2. temperaturewith cooling for 30 minutes after which time it
  3. washwashed with water, and brine (2X)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation in vacuo to dryness
  6. customprovided a residue which
  7. customwas chromatographed on silica gel using a toluene-ethyl acetate gradient
  8. customto give 0.194 g

Sources & evidence

ORD record
ord-29c9cdc8c807469189e01801fc6709bb
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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