Tetrahydrofuran → HCID 70635434, compound

HRID 1730863Notes

Reaction equation

HRID 1730863 reaction equation
[O:1]1CCC[CH2:2]1.C[Li].[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][C:14]([NH:16][CH:17]1[C:37](=[O:38])[N:19]2[C:20]([C:29]([O:31][CH2:32][O:33][C:34](=[O:36])[CH3:35])=[O:30])=[C:21]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH2:22][S:23][C@H:18]12)=[O:15].C(OCl)(C)(C)C>CCOCC.C(O)(=O)C.CO>[CH3:2][O:1][C:17]1([NH:16][C:14](=[O:15])[CH2:13][C:9]2[S:8][CH:12]=[CH:11][CH:10]=2)[C:37](=[O:38])[N:19]2[C:20]([C:29]([O:31][CH2:32][O:33][C:34](=[O:36])[CH3:35])=[O:30])=[C:21]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH2:22][S:23][C@H:18]12

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 521297Tert-Butyl hypochloriteHCID 131710533HCID 131710533, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 70635434HCID 70635434, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To 25 ml of tetrahydrofuran was added 2 ml of a 1.8 molar solution of methyl lithium in ether. The solution was cooled to 0° C. and 4 ml of methanol were added to the solution. The solution was then cooled to -80° C and 468 mg of acetoxymethyl 7-[2-(2-thienyl)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylate were added, followed by the addition of 0.143 ml of t-butylhypochlorite. The cold reaction mixture was stirred for 25 minutes and was thereafter diluted with 4 ml of glacial acetic acid. The acidified reaction mixture was evaporated to dryness and the residual reaction product mixture was dissolved in dichloromethane. The solution was washed consecutively with a saturated solution of sodium chloride, a dilute solution of sodium thiosulfate, a saturated solution of sodium bicarbonate, and finally with a saturated solution of sodium chloride. The washed solution was dried and was then evaporated to dryness. The residue was chromatographed on preparative thin layer silica gel plates using benzene-ethyl acetate (7:3). The location of separated materials on the chromatogram was determined with an ultraviolet lamp. The reaction product was eluted from the silica gel with acetone. The acetone was evaporated to yield 202 mg of acetoxymethyl 7-methoxy-7-[2-(2-thienyl)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylate.

Workup

  1. temperatureThe solution was then cooled to -80° C
  2. customThe cold reaction mixture
  3. customThe acidified reaction mixture
  4. customwas evaporated to dryness
  5. dissolutionthe residual reaction product mixture was dissolved in dichloromethane
  6. washThe solution was washed consecutively with a saturated solution of sodium chloride
  7. customThe washed solution was dried
  8. customwas then evaporated to dryness
  9. customThe residue was chromatographed on preparative thin layer silica gel plates
  10. customThe location of separated materials on the chromatogram was determined with an ultraviolet lamp
  11. washThe reaction product was eluted from the silica gel with acetone
  12. customThe acetone was evaporated

Sources & evidence

ORD record
ord-0baf3da1789e4964acfe2a24be178700
Source dataset
uspto-grants-1976_11
Patent number
US03994885

Reaction notes

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