Potassium Carbonate → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

HRID 132945Notes

Reaction equation

FC1C=C(C=C(F)C=1)C[C@H]1[C@@H]([C@H]2CCCCN2C(C2C=CC=CC=2)C2C=CC=CC=2)OC(=O)N1.[F:35][C:36]1[CH:37]=[C:38]([CH:65]=[C:66]([F:68])[CH:67]=1)[CH2:39][C@H:40]1[C@@H:44]([C@H:45]2[CH2:50][O:49][CH2:48][CH2:47][N:46]2[CH:51]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:43][C:42](=[O:64])[NH:41]1.FC1C=C(C=C(F)C=1)C[C@@H]([C@@H]([C@H]1C[C@@H](OCC=C)CN1C(OC(C)(C)C)=O)O)C(O)=O.C(=O)([O-])[O-].[K+].[K+].BrC(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[F:35][C:36]1[CH:37]=[C:38]([CH:65]=[C:66]([F:68])[CH:67]=1)[CH2:39][C@H:40]1[C@@H:44]([C@H:45]2[CH2:50][C@H:48]([OH:49])[CH2:47][N:46]2[CH:51]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[O:43][C:42](=[O:64])[NH:41]1

Participants

Conditions

Temperature: 100 °C

Procedure

Step L (7): (4S,5S)-4-(3,5-Difluorobenzyl)-5-((R)-4-benzhydrylmorpholin-3-yl)oxazolidin-2-one. To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-(morpholin-3-yl)oxazolidin-2-one (step L (6), 180 mg, 0.6 mmol) in acetonitrile (5 mL) were added potassium carbonate (248 mg, 1.8 mmol) and bromodiphenylmethane (296 mg, 1.2 mmol). This mixture was stirred at 100° C. for 1.5 h. Solvent was removed and the crude mixture was purified by silica gel Flash Chromatography (0% to 20% to 40% to 65% EtOAc/Hexane step gradient) to give 85 mg of the title compound (29% yield):

Workup

customSolvent was removed
customthe crude mixture was purified by silica gel Flash Chromatography (0% to 20% to 40% to 65% EtOAc/Hexane step gradient)

Sources & evidence

ORD record: ord-b9c564c842224d0691e37a8553f9a9c6
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07388007B2

Reaction notes

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