Diethyl Ether → HCID 14672406, compound

HRID 2073676Notes

Reaction equation

HRID 2073676 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[I-].[Na+].C(OCC)C.[NH2:17][C:18]1[S:19][CH:20]=[C:21](/[C:23](=[N:49]/[O:50][CH3:51])/[C:24]([NH:26][C@@H:27]2[C:47](=[O:48])[N:29]3[C:30]([C:44]([O-:46])=[O:45])=[C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=4)[CH2:32][S:33][C@H:28]23)=[O:25])[N:22]=1.[Na+]>CC(C)=O.CN(C)C=O.C(OCC)(=O)C.O>[NH2:17][C:18]1[S:19][CH:20]=[C:21](/[C:23](=[N:49]/[O:50][CH3:51])/[C:24]([NH:26][C@@H:27]2[C:47](=[O:48])[N:29]3[C:30]([C:44]([O:46][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:45])=[C:31]([O:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([C:42]#[N:43])=[CH:40][CH:41]=4)[CH2:32][S:33][C@H:28]23)=[O:25])[N:22]=1

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 87885Chloromethyl pivalateHCID 23685256HCID 23685256, compound

Product 1

HCID 14672406HCID 14672406, compoundYield 21.2%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

57.4 mg (0.38 mmol) of chloromethyl pivalate was dissolved in 2 ml of acetone, and 63 mg (0.42 mmol) of sodium iodide was added thereto. The mixture was heated for 30 minutes at 50° C., and 4 ml of ethyl ether was added thereto. Insolubles were filtered off and the solvent was distilled off. Then, the residue was dissolved in 1 ml of N,N-dimethylformamide. 100 mg (0.217 mmol) of sodium 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-(4-cyanobenzyloxy)-3-cephem-4-carboxylate prepared in the same manner as in Example 12 was dissolved in 1 ml of N,N-dimethylformamide. The above solution was added to this solution under cooling with ice and stirred for 30 minutes at room temperature. Water and ethyl acetate was added to the reaction solution, and the ethyl acetate layer was separated and washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off and the residue was triturated with ethyl ether to obtain 24.8 mg (yield: 21.2%) of the above-identified compound.

Workup

  1. filtrationInsolubles were filtered off
  2. distillationthe solvent was distilled off
  3. dissolutionThen, the residue was dissolved in 1 ml of N,N-dimethylformamide
  4. additionThe above solution was added to this solution
  5. temperatureunder cooling with ice
  6. customthe ethyl acetate layer was separated
  7. washwashed sequentially with a saturated sodium hydrogencarbonate aqueous solution
  8. dry with materiala saturated sodium chloride aqueous solution and dried over magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-1070b3b5c7af4819bd8bf019e3e14737
Source dataset
uspto-grants-1990_04
Patent number
US04918070

Reaction notes

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