Acetonitrile → HCID 86592511, compound

HRID 1374396Notes

Reaction equation

HRID 1374396 reaction equation
[CH3:1][Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl:11][CH2:12][C@@H:13]1[CH2:18][C:17]([C:19]2[N:20]=[C:21]([SH:24])[S:22][CH:23]=2)=[CH:16][CH2:15][N:14]1[C:25]([O-:27])=[O:26].O(P(OC1C=CC=CC=1)O[C:37]1[C@H:43]([CH3:44])[C@H:42]2[N:39]([C:40](=[O:52])[C@@H:41]2[C@H:45]([O:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[CH3:46])[C:38]=1[C:53]([O:55][CH2:56][CH:57]=[CH2:58])=[O:54])C1C=CC=CC=1.[C:66](#N)[CH3:67]>C1COCC1>[CH2:1]([O:26][C:25]([N:14]1[CH2:15][CH:16]=[C:17]([C:19]2[N:20]=[C:21]([S:24][C:37]3[C@H:43]([CH3:44])[C@H:42]4[N:39]([C:40](=[O:52])[C@@H:41]4[C@H:45]([O:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[CH3:46])[C:38]=3[C:53]([O:55][CH2:56][CH:57]=[CH2:58])=[O:54])[S:22][CH:23]=2)[CH2:18][C@H:13]1[CH2:12][Cl:11])=[O:27])[CH:66]=[CH2:67]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 2733832Lithium HexamethyldisilazideHCID 86592502HCID 86592502, compoundHCID 178526058HCID 178526058, compound

Product 1

HCID 86592511HCID 86592511, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium hexamethyldisilazide in THF (1M, 0.19 ml, 0.19 mmol) was added at 0° C. to a solution of (2S)-2-(chloromethyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (64 mg, 0.19 mmol) in THF (11.0 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%, 0.74 g, 0.38 mmol) and the solution was allowed to stand in a refrigerator for 15 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-[(2S)-1-[(allyloxy)carbonyl]-2-(chloromethyl)-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 (54 mg, 43%).

Workup

  1. waitto stand in a refrigerator for 15 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-b2ee8779446f4ae28bcda7f77e7cd864
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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