Ethyl difluoroacetate → HCID 10340972, compound

HRID 2213372Notes

Reaction equation

C(O[C:6](=[O:30])[NH:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([N:22]3[CH:27]=[CH:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[C:17]([F:29])[CH:16]=2)[CH2:10]1)(C)(C)C.[F:31][CH:32]([F:38])C(OCC)=O>>[F:21][C:19]1[CH:20]=[C:15]([N:11]2[CH2:10][CH:9]([CH2:8][NH:7][C:6](=[O:30])[CH:32]([F:38])[F:31])[O:13][C:12]2=[O:14])[CH:16]=[C:17]([F:29])[C:18]=1[N:22]1[CH:27]=[CH:26][C:25](=[O:28])[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 9961Ethyl difluoroacetate

HCID 21051177HCID 21051177, compound

Product 1

HCID 10340972HCID 10340972, compound

Procedure

The compound is prepared from {3-[3,5-difluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid tert-butyl ester (402 mg, 0.92 mmol) and ethyl difluoroacetate (360 mg, 2.88 mmol) following the method described in example 9. The crude product is purified by silica gel column chromatography (eluent: EtOAc) to give a white solid. Yield 68 mg (18%). MS (m/z): 402 [M+1]+. 1H NMR (300 MHz, DMSO-d6): 9.16 (br. t, 1H), 7.46–7.38 (m, 3H), 6.24 (dd, J=11.0 and 14.8 Hz, 1H), 4.99 (d, J=7.4 Hz, 1H), 4.85–4.81 (m, 1H), 4.15 (t, J=9.3 Hz, 1H), 3.81–3.74 (m, 3H), 3.52 (t, J=5.5 Hz, 2H), 2.48 (m, 2H).

Workup

customThe crude product is purified by silica gel column chromatography (eluent: EtOAc)
customto give a white solid

Sources & evidence

ORD record: ord-aea503db04f645f1b3880f272e91b7f2
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105547B2

Reaction notes

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