Dimethylformamide → HCID 178431941, compound

HRID 1764382Notes

Reaction equation

HRID 1764382 reaction equation
Br[CH2:2][C:3]([NH:5][CH:6]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:7]([NH:9][CH:10]1[C:23](=[O:24])[N:12]2[CH:13]([C:18]3[NH:22][N:21]=[N:20][N:19]=3)[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]12)=[O:8])=[O:4].CN(C)C=O.[SH:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:40]1[CH:41]=[CH:42][C:37]([S:36][CH2:2][C:3]([NH:5][CH:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]([NH:9][CH:10]2[C:23](=[O:24])[N:12]3[CH:13]([C:18]4[NH:22][N:21]=[N:20][N:19]=4)[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]23)=[O:8])=[O:4])=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 178418431pyridine-4-thiolHCID 178431939HCID 178431939, compound

Product 1

HCID 178431941HCID 178431941, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 644 mg. of 6-(2-[2-bromoacetamido]-2-phenylacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam in 15 ml. of N,N-dimethylformamide is added 45 mg. of 4-mercaptopyridine followed by 0.19 ml. of triethylamine. Stirring is continued for 3 hours at 25° C., and then the reaction solution is added dropwise into 200 ml. of vigorously stirred chloroform. The precipitate is removed by filtration, and the filtrate is added dropwise with stirring to 400 ml. of hexane. This causes the product to precipitate. After being slurried with methylene chloride, it weighs 228 mg. (33% yield), m.p. 182°-198° C. (dec.). IR (KBr disc): 1780 cm-1 (β-lactam) and 1667 cm-1 (amide I). NMR (DMSO-d6 /D2O): 8.33 ppm (d,4H), 7.33 (s,5H), 5.60 ppm (m, 3H), 5.15 ppm (s,1H), 3.68 ppm (s,2H), 1.47 ppm (s,3H), 1.00 ppm (s,3H).

Workup

  1. additionthe reaction solution is added dropwise into 200 ml
  2. customThe precipitate is removed by filtration
  3. additionthe filtrate is added dropwise
  4. stirringwith stirring to 400 ml
  5. customto precipitate

Sources & evidence

ORD record
ord-d70b4f6db69e4ed9a9a77f3652bae9fe
Source dataset
uspto-grants-1978_09
Patent number
US04115385

Reaction notes

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