4-Methylmorpholine → Penicillanic Acid

HRID 616244Notes

Reaction equation

HRID 616244 reaction equation
CN1CCOCC1.S(Cl)(Cl)=O.[CH3:12][C:13]1([CH3:25])[S:17][C@@H:16]2[C@H:18](N)[C:19](=[O:20])[N:15]2[C@H:14]1[C:22]([OH:24])=[O:23]>CN(C)C=O.O>[CH3:12][C:13]1([CH3:25])[S:17][C@@H:16]2[CH2:18][C:19](=[O:20])[N:15]2[C@H:14]1[C:22]([OH:24])=[O:23]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 110826-Aminopenicillanic acidHCID 24386Thionyl Chloride

Product 1

HCID 6891Penicillanic AcidYield 6.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 3.12 g. of 4-pyridylformimidoylglycyl-d-phenylglycine in 40 ml. of dimethylformamide cooled to -20° C. is added 1.0 g. of N-methylmorpholine followed by 1.2 g. of thionyl chloride. The resulting clear solution is stirred for 45 min. at -15° to -20° C., and is subsequently treated with 2.16 g. of 6-aminopenicillanic acid in 20 ml. of water, 10 ml. of dimethylformamide at pH 7.8. After allowing the reaction mixture to stir for 10 min. at -10° C., it is allowed to warm to room temperature. High-pressure-liquid-chromatography of the solution indicates a yield of 335 mg. of 6- D-2-phenyl-2-(4-pyridylformimidoylaminoacetamido)acetamido!penicillanic acid (6.5% yield).

Workup

  1. additionis added 1.0 g
  2. additionis subsequently treated with 2.16 g
  3. stirringto stir for 10 min. at -10° C.

Sources & evidence

ORD record
ord-9f67d6ee7e544c92ac4c0b276ae30914
Source dataset
uspto-grants-1978_02
Patent number
US04073780

Reaction notes

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