Acetonitrile → HCID 10875843, compound

HRID 1374386Notes

Reaction equation

HRID 1374386 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][C@@H:12]1[N:17]([C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[CH2:16][CH2:15][C:14]([C:24]2[N:25]=[C:26]([SH:29])[S:27][CH:28]=2)=[CH:13]1.O(P(OC1C=CC=CC=1)O[C:39]1[C@H:45]([CH3:46])[C@H:44]2[N:41]([C:42](=[O:54])[C@@H:43]2[C@H:47]([O:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[CH3:48])[C:40]=1[C:55]([O:57][CH2:58][CH:59]=[CH2:60])=[O:56])C1C=CC=CC=1.C(#N)C>C1COCC1>[CH2:21]([O:20][C:18]([N:17]1[C@@H:12]([CH3:11])[CH:13]=[C:14]([C:24]2[N:25]=[C:26]([S:29][C:39]3[C@H:45]([CH3:46])[C@H:44]4[N:41]([C:42](=[O:54])[C@@H:43]4[C@H:47]([O:49][Si:50]([CH3:51])([CH3:52])[CH3:53])[CH3:48])[C:40]=3[C:55]([O:57][CH2:58][CH:59]=[CH2:60])=[O:56])[S:27][CH:28]=2)[CH2:15][CH2:16]1)=[O:19])[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 2733832Lithium HexamethyldisilazideHCID 86592502HCID 86592502, compoundHCID 178459660HCID 178459660, compound

Product 1

HCID 10875843HCID 10875843, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hexamethyldisilazide in THE (1M, 1.26 ml, 1.26 mmol) was added at 0° C. to a solution of allyl (6S)-6-methyl-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2H)-pyridine carboxylate (373 mg, 1.26 mmol) in THF (15 ml) and the mixture was stirred for 10 minutes. To the reaction solution was added at 0° C. a solution of allyl (4R,5R,6S)-3-[(diphenoxyphosphino)oxy]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate in acetonitrile (30%, 4.80 g, 2.52 mmol) and the solution was allowed to stand in a refrigerator for 60 hours. To the reaction solution was added ice water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the solvent in vacuo, the residue was purified with silica gel chromatography (hexane/ethyl acetate) to give allyl (4R,5S,6S)-3-[(4-{(6S)-1-[(allyloxy)carbonyl]-6-methyl-1,2,3,6-tetrahydro-4-pyridinyl}-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (590 mg, 76%).

Workup

  1. waitto stand in a refrigerator for 60 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent in vacuo
  6. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7e1ac0ac78384c39af4f2c324df1d631
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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