Acetic Acid → HCID 10238059, compound

HRID 2306627Notes

Reaction equation

OO.[F:3][C:4]1[CH:5]=[C:6]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]2=[O:27])[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=1.[C:28]([OH:31])(=[O:30])[CH3:29]>>[C:24]([NH:23][CH2:22][C@@H:20]1[O:19][C:18](=[O:27])[N:17]([C:6]2[CH:7]=[CH:8][C:9]([C:10]3[S:11][CH:12]([O:31][C:28](=[O:30])[CH3:29])[C:13](=[O:16])[NH:14][N:15]=3)=[C:4]([F:3])[CH:5]=2)[CH2:21]1)(=[O:26])[CH3:25]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 784Hydrogen Peroxide

HCID 10309167HCID 10309167, compound

Product 1

HCID 10238059HCID 10238059, compoundYield 82%

Conditions

Temperature: 65 °C

Procedure

Hydrogen peroxide (30% aqueous sol, 0.0558 ml, 0.546 mmol) is added to N-{3-[3-Fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide (0.100 g, 0.273 mmol) in acetic acid (2 ml) and is heated at 65° C. overnight. The reaction mixture is evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give white solid (0.089 g, 82%); 1HNMR (300 MHz, DMSO-d6) δ 1.82 (s, 3H), 2.09 (s, 3H), 3.41 (t, J=5.5 Hz, 2H), 3.56 (dd, J=6.6, 9.1 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.70-4.80 (m, 1H), 7.42 (dd, J=2.2, 8.8 Hz, 1H), 7.59 (dd, J=2.2, 14 Hz, 1H), 7.65 (t, J=8.5 Hz, 1H), 8.25 (t, J=5.8 Hz, 1H); mp 174-7; MS (m/z): [M+H]+=425.

Workup

customThe reaction mixture is evaporated to dryness
customthe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record: ord-1420f7c369b347dba3cfa9b55dbd8128
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828317B2

Reaction notes

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