Bromoacetic Acid → HCID 178431939, compound

HRID 614154Notes

Reaction equation

HRID 614154 reaction equation
[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[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].[Br:27][CH2:28][C:29](O)=[O:30].Cl.C(N=C=NCCCN(C)C)C>O>[Br:27][CH2:28][C:29]([NH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[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:30]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178431936HCID 178431936, compound

Product 1

HCID 178431939HCID 178431939, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a stirred slurry of 4.27 g. (10 mmole) of 6-(2-amino-2-phenylacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam in 25 ml. of water, at 0° C., is added 1.39 g. (10 mmole) of bromoacetic acid in 6 ml. of water. The pH is adjusted to 6.0, and then 1.9 g. (10 mmole) of 1-ethyl-3-(dimethylaminopropyl)-carbodimide hydrochloride in 9 ml. of water is added. The mixture is stirred for 3 hours at pH 6. At this point, the pH is raised to 7.0, and the reaction mixture is washed with ethyl acetate. The pH is then lowered to 2.0, and the product is extracted into ethyl acetate. The dried extracts are concentrated to dryness in vacuo to give 2.0 g. (40% yield) of the title compound, m.p. 128°-135° C. IR (KBr disc): 1800 cm-1 (β-lactam) and 1653 cm-1 (amide I). NMR (in DMSO-d6 /D2O): 7.43 ppm (s, 5H), 5.73 ppm (s, 1H), 5.63 ppm (m, 2H), 5.23 ppm (s, 1H), 4.02 ppm (s, 2H), 1.60 ppm (s, 3H), 1.00 ppm (s, 3H).

Workup

  1. temperatureAt this point, the pH is raised to 7.0
  2. washthe reaction mixture is washed with ethyl acetate
  3. extractionthe product is extracted into ethyl acetate
  4. concentrationThe dried extracts are concentrated to dryness in vacuo
  5. customto give 2.0 g

Sources & evidence

ORD record
ord-6cc5bad36c324da0986e2712320292a6
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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