Triethylamine → 3-(Acetyloxy)methyl-7-[[4-(1-pyrryl)butyryl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid

HRID 26318

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[C:27]([O:30][CH2:31][C:32]1[CH2:39][S:38][CH:37]2[N:34]([C:35](=[O:41])[CH:36]2[NH2:40])[C:33]=1[C:42]([OH:44])=[O:43])(=[O:29])[CH3:28]>O1CCCC1.O>[C:27]([O:30][CH2:31][C:32]1[CH2:39][S:38][CH:37]2[N:34]([C:35](=[O:41])[CH:36]2[NH:40][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][N:1]2[CH:2]=[CH:3][CH:4]=[CH:5]2)[C:33]=1[C:42]([OH:44])=[O:43])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: -10 °C

Procedure

4-(1-Pyrryl)butanoic acid (0.05 mole) is dissolved in 50 ml of tetrahydrofuran (THF) and 0.05 mole of triethylamine is added. This mixture is cooled to -10° C. and 0.05 mole of isobutylchloroformate is added. The mixture is stirred for 0.5 hours at -5° C. and then 0.05 mole of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 0.075 mole of triethyl amine in 50 ml of THF (precooled) is added. The mixture is stirred at 0° C. for 1 hour and then warmed to room temperature. The mixture is diluted with water and extracted with ethyl acetate. The aqueous layer is acidified and extracted with ethyl acetate. The ethyl acetate extracts are combined, dried, filtered, and the solvent evaporated to give the title compound.

Workup

stirringThe mixture is stirred at 0° C. for 1 hour
temperaturewarmed to room temperature
extractionextracted with ethyl acetate
extractionextracted with ethyl acetate
customdried
filtrationfiltered
customthe solvent evaporated

Sources & evidence

ORD record: ord-6631c8a00d354e8eb16797c3c5063d19
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148998

Linked notes

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