Water → HCID 178431938, compound

HRID 614153Notes

Reaction equation

HRID 614153 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]1[C:19](=[O:20])[N:8]2[CH:9]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[C:10]([CH3:13])([CH3:12])[S:11][C@H:7]12)=[O:4].C(=O)(O)[O-].[Na+].O.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)=O>[C:27]([NH:1][CH2:2][C:3]([NH:5][CH:6]1[C:19](=[O:20])[N:8]2[CH:9]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[C:10]([CH3:13])([CH3:12])[S:11][C@H:7]12)=[O:4])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 178431942HCID 178431942, compound

Product 1

HCID 178431938HCID 178431938, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 0.80 g. (2.7 mmole) of 6-(2-aminoacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam and 0.453 g. (5.4 mmole) of sodium bicarbonate in 21 ml. of water and 15 ml. of acetone at 0°-5° C. is added 0.32 ml. (2.8 mmole) of benzoyl chloride. Starting is continued for a further 20 minutes at ca. 0° C., and then the acetone is removed in vacuo. The aqueous residue is extracted with ethyl acetate and the extracts are discarded. The pH of the aqueous phase is adjusted to 2.0, and the product is extracted into ethyl acetate. The solvent is dried (Na2SO4), and then concentrated in vacuo to give 150 mg. (37% yield) of the title compound, m.p. 85°-93° C. IR (KBr disc): 1785 cm-1 (β-lactam) and 1695 cm-1 (amide I). NMR (in D2O): 7.90 ppm (m, 2 H), 7.50 ppm (m, 3H), 5.82 ppm (s, 1H), 5.58 ppm (s, 1H), 5.19 ppm (s, 1), 4.25 ppm (m, 2H), 1.67 ppm (s, 3H), 1.67 ppm (s, 1H).

Workup

  1. customthe acetone is removed in vacuo
  2. extractionThe aqueous residue is extracted with ethyl acetate
  3. extractionthe product is extracted into ethyl acetate
  4. dry with materialThe solvent is dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give 150 mg

Sources & evidence

ORD record
ord-705d88c305c9481b904e261bfc988ea7
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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