Triethylamine → HCID 68123060, compound

HRID 1438792Notes

Reaction equation

HRID 1438792 reaction equation
Cl.[Br:2][CH2:3][CH2:4][C:5]1([CH3:22])[CH:9]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])[N:8]2[C:18](=[O:21])[CH:19]([NH2:20])[C@H:7]2[S:6]1.C(N(CC)CC)C.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:41]([C:42](Cl)=[O:43])=[C:40]([CH3:45])[O:39][N:38]=1>C(Cl)Cl>[Br:2][CH2:3][CH2:4][C:5]1([CH3:22])[CH:9]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])[N:8]2[C:18](=[O:21])[CH:19]([NH:20][C:42]([C:41]3[C:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[Cl:30])=[N:38][O:39][C:40]=3[CH3:45])=[O:43])[C@H:7]2[S:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 965904-Isoxazolecarbonyl chloride, 3-(2-chlorophenyl)-5-methyl-HCID 68123647HCID 68123647, compound

Product 1

HCID 68123060HCID 68123060, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,2,2-trichloroethyl 2-bromoethyl-2-methyl-6-aminopenam-3-carboxylate hydrochloride (6.95 g) and triethylamine (3.0 g) in dried methylene chloride (100 ml) was cooled at -25° C. To this solution was added dropwise a solution of 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride (4.5 g) in dried methylene chloride (30 ml), and the mixture was stirred for 33 hours at the same temperature. After the reaction was completed, the reaction mixture was post-treated in the similar manner as described in Example 1 to give oily 2,2,2-trichloroethyl 2-bromoethyl-2-methyl-6-[3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido]penam-3-carboxylate (6.75 g).

Workup

  1. additionthe reaction mixture was post-treated in the similar manner

Sources & evidence

ORD record
ord-450f58c6ab5e4b2c9995fd34dfdde689
Source dataset
uspto-grants-1977_11
Patent number
US04056521

Reaction notes

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