Acetonitrile → HCID 131722900, compound

HRID 382607Notes

Reaction equation

HRID 382607 reaction equation
[C:1]([Si:5]([CH3:33])([CH3:32])[O:6][C@@H:7]([C@H:9]1[C:30](=[O:31])[N:11]2[C@@H:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])[C:13](=O)[C@H:14]([CH3:15])[C@H:10]12)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:34]([N:37]([CH2:41]C)[CH:38](C)C)(C)[CH3:35].F[C:44](F)(F)[S:45](O)(=O)=O.C(=O)([O-])O.[Na+].C(#[N:58])C>C(OCC)(=O)C>[Si:5]([O:6][C@@H:7]([C@H:9]1[C:30](=[O:31])[N:11]2[C:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])=[C:13]([C:44]3[S:45][C:34]4=[CH:35][N:58]=[CH:41][N:37]4[CH:38]=3)[C@H:14]([CH3:15])[C@H:10]12)[CH3:8])([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:32])[CH3:33]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 62406Trifluoromethanesulfonic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11754753HCID 11754753, compound

Product 1

HCID 131722900HCID 131722900, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 292 mg of 4-nitro-benzyl (1R,3R,5R,6S)-6-[(1R)-1-(t-butyldimethyl-silyloxy)ethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 8 ml of dry acetonitrile was ice-cooled under the atmosphere of argon, and 0.267 ml of N,N-diisopropylethylamine was added dropwise, followed by 0.103 ml of anhydrous trifluoromethanesulfonic acid. After the reaction mixture was stirred at the same temperature for 30 minutes, it was diluted with ethyl acetate, a mixture of semi-saturated aqueous saline saturated aqueous sodium hydrogen carbonate (pH 8.9), and semi-saturated aqueous saline in this sequence. The organic layer was dried over anhydrous magnesium sulfate, filtered, mixed with 3 ml of N-methylpyrrolidinone, and the ethyl acetate was removed under reduced pressure. The residue was mixed with 17 mg of tris(dibenzylideneacetone)dipalladium (0), 17 mg of tri-2-furylphosphine, 376 mg of 2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole in 1 ml of dry N-methylpyrrolidinone, and 167 mg of zinc chloride, and the mixture was stirred under the atmosphere of argon at 50° C. for 4 hours. The reaction mixture was diluted with ethyl acetate, and washed with semi-saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (ethyl acetate) and on Sephadex LH-20 (chloroform:methanol=1:1) in this sequence to give 111 mg of 4-nitrobenzyl (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. additionwas added dropwise
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. additionmixed with 3 ml of N-methylpyrrolidinone
  5. customthe ethyl acetate was removed under reduced pressure
  6. additionThe residue was mixed with 17 mg of tris(dibenzylideneacetone)dipalladium (0), 17 mg of tri-2-furylphosphine, 376 mg of 2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole in 1 ml of dry N-methylpyrrolidinone, and 167 mg of zinc chloride
  7. stirringthe mixture was stirred under the atmosphere of argon at 50° C. for 4 hours
  8. additionThe reaction mixture was diluted with ethyl acetate
  9. washwashed with semi-saturated aqueous saline
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified by column chromatography on silica gel (ethyl acetate) and on Sephadex

Sources & evidence

ORD record
ord-04e5131126df422b8c0c01ca1b9e801e
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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