Acetic Acid → HCID 58237533, compound

HRID 885363Notes

Reaction equation

COC(=O)CO[C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[CH2:25][N:26]2[C@H:30]([CH3:31])[C@H:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:28][C:27]2=[O:38])[CH:7]=1.Br.[C:41]([OH:44])(=[O:43])[CH3:42]>>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:42][C:41]([OH:44])=[O:43])=[CH:7][C:8]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][C:16]=1[CH2:25][N:26]1[C@H:30]([CH3:31])[C@H:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:28][C:27]1=[O:38]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 67105560HCID 67105560, compound

Product 1

HCID 58237533HCID 58237533, compound

Conditions

Temperature: 100 °C

Procedure

{4-Methoxy-3-[2-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenoxy}-acetic acid methyl ester (2.0 g, 3.78 mmol) was treated with a 1:1 mixture of 48% hydrogen bromide and acetic acid, and the reaction was heated to 100° C. overnight. The mixture was concentrated to dryness, and then worked-up with EtOAc and saturated aqueous NaHCO3. The crude material was purified by silica gel chromatography to give the title compound.

Workup

concentrationThe mixture was concentrated to dryness
customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-a5c3ec41ceb34c86890bf4e48f5e4c3e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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