Acetic Acid → HCID 58781936, compound

HRID 1374401Notes

Reaction equation

HRID 1374401 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[C:14]([C:15]2[N:16]=[C:17]([S:20][C:21]3[C@H:27]([CH3:28])[C@H:26]4[N:23]([C:24](=[O:36])[C@@H:25]4[C@H:29]([O:31][Si](C)(C)C)[CH3:30])[C:22]=3[C:37]([O:39]CC=C)=[O:38])[S:18][CH:19]=2)=[CH:13][CH2:12][N:11]1[CH3:43])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[OH:31][C@@H:29]([C@H:25]1[C:24](=[O:36])[N:23]2[C@@H:26]1[C@@H:27]([CH3:28])[C:21]([S:20][C:17]1[S:18][CH:19]=[C:15]([C:14]3[C@H:10]([CH2:9][OH:8])[N:11]([CH3:43])[CH2:12][CH:13]=3)[N:16]=1)=[C:22]2[C:37]([OH:39])=[O:38])[CH3:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86592515HCID 86592515, compound

Product 1

HCID 58781936HCID 58781936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of allyl (4R,5S,6S)-3-({4-[(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-methyl-2,5-dihydro-1H-pyrrol-3-yl]-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(106 mg, 0.16 mmol) in THF (2.7 ml) was cooled at 0° C. and to the solution were added acetic acid (0.073 ml, 1.28 mmol) and tetrabutylammonium fluoride in THF (1M, 0.64 ml, 0.64 mmol). The solution was stirred at the same temperature for 1 hour and then was allowed to stand in a refrigerator for 63 hours. To the reaction mixture was added water, and the solution was extracted three times 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 and then was subjected to de-allyl reaction in the same manner as Example 1.c) to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-({4-[(2R)-2-hydroxymethyl-1-methyl-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Workup

  1. waitto stand in a refrigerator for 63 hours
  2. extractionthe solution was extracted three times 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
  7. customwas subjected to de-allyl reaction in the same manner as Example 1.c)

Sources & evidence

ORD record
ord-dfd089b32a0a43e0a95d7861603c61e8
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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