Acetonitrile → Faropenem Related Compound 1

HRID 2393729Notes

Reaction equation

HRID 2393729 reaction equation
C(#N)C.[Si:4]([O:11][C@@H:12]([C@@H:14]1[C@@H:17](SC2C=CC=CC=2)[NH:16][C:15]1=[O:25])[CH3:13])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].[O:26]1[CH2:30][CH2:29][CH2:28][C@@H:27]1[C:31](=[S:33])[OH:32]>[Cu-]=O.C1(C)C=CC=CC=1>[Si:4]([O:11][C@@H:12]([C@@H:14]1[C@@H:17]([S:33][C:31]([C@H:27]2[CH2:28][CH2:29][CH2:30][O:26]2)=[O:32])[NH:16][C:15]1=[O:25])[CH3:13])([C:7]([CH3:10])([CH3:8])[CH3:9])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 11089029HCID 11089029, compoundHCID 178526199HCID 178526199, compound

Product 1

HCID 10872089Faropenem Related Compound 1

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1140TolueneSolvent

Procedure

15 ml of acetonitrile, 15 ml of toluene and 0.8 g of copper (I) oxide (5.6 mmol) were added to (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-phenylthio-2-azetidinone (2.7 g, 8.0 mmol), and (2R)-tetrahydrofuran-2-thiocarboxylic acid (1.2 g, 9.1 mmol) was added dropwise into the resulting mixture at 10° C. while being stirred.

Workup

  1. additionwas added dropwise into the resulting mixture at 10° C.

Sources & evidence

ORD record
ord-3163f1ecc8544ebba63a8daae7dd2b2e
Source dataset
uspto-grants-1998_09
Patent number
US05808055

Reaction notes

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