Ethyl Acetate → N-[((5S)-3-{4'-[(5R)-5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

HRID 747240Notes

Reaction equation

HRID 747240 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C@@H:28]1[O:32][N:31]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([N:45]4[CH2:49][C@H:48]([CH2:50][NH:51][C:52](=[O:54])[CH3:53])[O:47][C:46]4=[O:55])=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)[CH2:29]1)(C(C)(C)C)(C)C.C(OCC)(=O)C>C1COCC1>[OH:26][CH2:27][C@@H:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[CH:35][C:36]([C:39]3[CH:40]=[CH:41][C:42]([N:45]4[CH2:49][C@H:48]([CH2:50][NH:51][C:52](=[O:54])[CH3:53])[O:47][C:46]4=[O:55])=[CH:43][CH:44]=3)=[CH:37][CH:38]=2)[CH2:29]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 59749465N-[((5S)-3-{4'-[(5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

Product 1

HCID 59749523N-[((5S)-3-{4'-[(5R)-5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamideYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride in THF (1M, 0.69 ml, 0.69 mM) was added to a solution of N-[((5S)-3-{4′-[(5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1′-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide (300 mg, 0.57 mM) in THF (5 ml). After approximately 2 hours, ethyl acetate was added and the resulting suspension was filtered. The filter cake was washed with water and ethyl acetate to give 140 mg of the title product.

Workup

  1. filtrationthe resulting suspension was filtered
  2. washThe filter cake was washed with water and ethyl acetate

Sources & evidence

ORD record
ord-286f1ef29f614d34afa2967716e1e9b4
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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