Bromoacetic Acid → HCID 178431939, compound

HRID 1448390Notes

Reaction equation

HRID 1448390 reaction equation
[NH2:1][C:2](N)([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:28][CH2:29][C:30](O)=[O:31].Cl.C(N=C=NCCCN(C)C)C>O>[Br:28][CH2:29][C:30]([NH:1][CH:2]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=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]([CH3:12])([CH3:13])[S:11][C@H:7]12)=[O:4])=[O:31]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178431945HCID 178431945, 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-2amino-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), 160 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-ad258db265d94549a81e1380f3124a94
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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