Cesium carbonate → 1-((4S,5R)-5-(4-(6-(2-oxa-5-azaspiro[3.4]octan-5-ylmethyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-3-yl)-2,2-difluoroethanone

HRID 1487571Notes

Reaction equation

[CH2:1]1[C:4]2([CH2:8][CH2:7][CH2:6][NH:5]2)[CH2:3][O:2]1.Cl[CH2:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C@H:23]3[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:34])[CH:31]([F:33])[F:32])[C@@H:24]3[CH2:35][F:36])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:3]1[C:4]2([CH2:8][CH2:7][CH2:6][N:5]2[CH2:10][C:11]2[N:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C@H:23]4[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:34])[CH:31]([F:33])[F:32])[C@@H:24]4[CH2:35][F:36])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:1][O:2]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 2-oxa-5-azaspiro[3.4]octane (0.1 mmol, 15.8 mg), 1-{(4S,5R)-5-[4-(6-Chloromethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone (Example 99, Step 2, 0.09 mmol, 37 mg) and cesium carbonate (0.25 mmol, 81 mg) and acetonitrile (1 mL) was heated to 55° C. for 5 hours. The crude mixture was filtered on a bed of celite and the cake was washed with CH2Cl2 (2 mL). The volatiles were removed. The crude mixtures were used “as is” in step 2.

Workup

filtrationThe crude mixture was filtered on a bed of celite
washthe cake was washed with CH2Cl2 (2 mL)
customThe volatiles were removed

Sources & evidence

ORD record: ord-a3308aab0f354aeab067d0c9aad3684f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428528B2

Reaction notes

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