ChemicalBook CAS DataBase List Side chain for meropenem

Side chain for meropenem synthesis

10synthesis methods

Product Name:Side chain for meropenem
CAS Number:96034-64-9
Molecular formula:C15H19N3O5S
Molecular Weight:353.39

1,2-Pyrrolidinedicarboxylic acid, 4-mercapto-, 1-[(4-nitrophenyl)methyl] ester, (2S,4S)-

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Yield:96034-64-9 92.3%

Reaction Conditions:

Stage #1: (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-carboxy-4-mercaptopyrrolidinewith N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 0 - 5; for 0.166667 h;
Stage #2: N,N-dimethylammonium chloride in N,N-dimethyl-formamide at 0 - 5; for 3 h;Concentration;

Steps:

10 Preparation of (2S, 4S) l-p-nitrobenzyloxycarbonyl-2- (N, N-dimethylcarbamoyl) -4-mercaptopyrrolidine (Formula VII)

The reaction flask was charged with 600 mL of DMF, and 179.5 g (0.55 mol) of (2S, 4S) -1- Carboxy-4-mercaptopyrrolidine (Formula VI) was prepared by reducing the temperature to 0 ° C to 5 ° C, adding 66.8 g (0.66 mol) Diisopropylethylamine, After stirring for 10 minutes, 89.7 g (1.10 mol) of dimethylamine hydrochloride was added and the mixture was stirred at 0 ° C to 5 ° C After 3 hours of reaction, 500 mL of purified ice water was quickly added, and a large amount of solid was precipitated under stirring. After filtration, the cake was washed with 200 mL of water , And dried under reduced pressure at 65 ° C for 15 hours to obtain 179.4 g of (2S, 4S) -1-p-nitrobenzyloxycarbonyl-2- (N, N-dimethylcarbamoyl Yl) -4-mercaptopyrrolidine (Formula VII), 92.3% molar yield, HPLC purity 99.3%. Compound VII mass spectrometry data are as follows: C15H19N3O5S, molecular weight: 353.4, [M + H] & lt; + & gt ;: 354.6.

References:

CN105439932,2016,A Location in patent:Paragraph 0075; 0076; 0077