Propionic anhydride → HCID 21957332, compound

HRID 2213371Notes

Reaction equation

C([O:5][C:6](=O)[NH:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:26]=[CH:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:10]1)(C)(C)C.[C:29](OC(=O)CC)(=O)[CH2:30]C>>[O:14]=[C:12]1[N:11]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:26]=[CH:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:10][CH:9]([CH2:8][NH:7][C:6](=[O:5])[CH2:29][CH3:30])[O:13]1

Participants

Reactant 2

HCID 31263Propionic anhydride

HCID 21051178HCID 21051178, compound

Product 1

HCID 21957332HCID 21957332, compound

Procedure

The compound is prepared from {3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid tert-butyl ester (232 mg, 0.60 mmol) and propionic anhydride (120 mg, 0.96 mmol) following the method described for Example 5. The crude product is purified by silica gel column chromatography (2% to 5% MeOH in EtOAc) to give the title compound as solid. MS (m/z): 344 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ8.16 (br. t, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.52 (d, J=7.1 Hz, 2H), 7.27 (d, J=7.4 Hz, 2H), 4.97 (d, J=7.4 Hz, 1H), 4.80–4.65 (m, 1H), 4.10 (t, J=7.7 Hz, 2H), 3.94 (t, J=6.9 Hz, 2H), 3.41–3.99 (m, 2H), 2.49–2.47 (m, 2H), 2.09 (q, J=5.8 Hz, 2H), 0.93 (t, J=7.4 Hz, 3H).

Workup

customThe crude product is purified by silica gel column chromatography (2% to 5% MeOH in EtOAc)

Sources & evidence

ORD record: ord-7cb5cf3b32f144a98c3fdbfd2fa373ba
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105547B2

Reaction notes

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