Triethylamine → HCID 178431944, compound

HRID 1448393Notes

Reaction equation

HRID 1448393 reaction equation
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:14][N:13]=[N:12][N:11]=3)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.C(N(CC)CC)C.Cl.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([NH:35][C:36](=[O:42])[NH:37][CH2:38][C:39](Cl)=[O:40])=[NH:34])=[CH:28][CH:27]=1>CN(C)C=O>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:35][C:36](=[O:42])[NH:37][CH2:38][C:39]([NH:1][CH:2]2[C:15](=[O:16])[N:4]3[CH:5]([C:10]4[NH:11][N:12]=[N:13][N:14]=4)[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]23)=[O:40])=[NH:34])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145793576HCID 145793576, compoundHCID 178431949HCID 178431949, compound

Product 1

HCID 178431944HCID 178431944, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 480 mg. of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam and 404 mg. of triethylamine, in 6 ml. of N,N-dimethylformamide, is added 650 mg. of 2-(3-[2-(p-chlorophenyl)acetimidoyl]ureido)acetyl chloride hydrochloride. Stirring is continued for 1 hour, and then the reaction mixture is filtered. The filtrate is added to 300 ml. of ether, and the solid which precipitates is filtered off. The solid is washed thoroughly with methylene chloride, and dried, giving 585 mg. of the title compound, m.p. 150°-162° C. IR spectrum (Nujol mull): 1780 cm-1 (β-lactam). NMR spectrum (DMSO-d6): 8.90 ppm (d, 1H), 8.00-7.20 ppm (m, 8H), 5.80-5.20 ppm (m, 3H), 4.10-3.60 ppm (m, 4H), 1.65 ppm (s, 3H), 1.10 ppm (s, 3H).

Workup

  1. filtrationthe reaction mixture is filtered
  2. additionThe filtrate is added to 300 ml
  3. customof ether, and the solid which precipitates
  4. filtrationis filtered off
  5. washThe solid is washed thoroughly with methylene chloride
  6. customdried
  7. customgiving 585 mg

Sources & evidence

ORD record
ord-24e7d73900194deda492cc0bfa227bb0
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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