Acetonitrile → HCID 86592516, compound

HRID 1374402Notes

Reaction equation

HRID 1374402 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][CH:12]1[CH2:17][CH:16]=[C:15]([C:18]2[N:19]=[C:20]([SH:23])[S:21][CH:22]=2)[CH2:14][N:13]1[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25].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>[CH2:27]([O:26][C:24]([N:13]1[CH:12]([CH3:11])[CH2:17][CH:16]=[C:15]([C:18]2[N:19]=[C:20]([S:23][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:21][CH:22]=2)[CH2:14]1)=[O:25])[CH:28]=[CH2:29]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 2733832Lithium HexamethyldisilazideHCID 86592502HCID 86592502, compoundHCID 178459644HCID 178459644, compound

Product 1

HCID 86592516HCID 86592516, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium hexamethyldisilazide in THF (1M, 1.24 ml, 1.24 mmol) was added at 0° C. to a solution of allyl 2-methyl-5-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (368 mg, 1.24 mmol) in THF (2.4 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%, 4.73 g, 2.5 mmol) and the solution was allowed to stand in a refrigerator for 13 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: 4/1→3/1) to give allyl (4R,5S,6S)-3-[(4-(1-[(allyloxy)carbonyl]-6-methyl-1,2,5,6-tetrahydro-3-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 (544 mg, 71%).

Workup

  1. waitto stand in a refrigerator for 13 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: 4/1→3/1)

Sources & evidence

ORD record
ord-aa42c5c6064f42f59440b12d5d7dc525
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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