Ethyl difluoroacetate → HCID 21957343, compound

HRID 2213370Notes

Reaction equation

HRID 2213370 reaction equation
C(OC(=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.[F:29][CH:30]([F:36])[C:31](OCC)=[O:32]>>[F:29][CH:30]([F:36])[C:31]([NH:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH:26]=[CH:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:19][CH:20]=2)[CH2:10]1)=[O:32]

Participants

3

Reactant 2

HCID 9961Ethyl difluoroacetate2×HCID 21051178HCID 21051178, compound

Product 1

HCID 21957343HCID 21957343, 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 (250 mg, 0.64 mmol) and ethyl difluoroacetate (120 mg, 0.96 mmol) following the method described for Example 5 (using ethyl difluoroacetate as starting agent). The product is purified by silica gel column chromatography (eluent 1% MeOH in EtOAc) and recrystallized from MeOH to provide the title compound. MS (m/z): 366 [M+1]. 1H NMR (300 MHz, DMSO) δ 9.16 (t, J=5.8 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.53 (d, J=9.1 Hz, 2H), 7.28 (d, J=9.1 Hz, 2H), 6.24 (t, J=53.0 Hz, 1H), 4.98 (d, J=7.7 Hz, 1H), 4.80–4.75 (m, 1H), 4.14 (t, J=9.1 Hz, 1H), 3.97–3.92 (m, 2H), 3.76 (dd, J=6.3 and 9.1 Hz, 1H), 3.52 (t, J=5.5 Hz, 2H), 2.47 (t, J=7.1 Hz, 2H).

Workup

  1. customThe product is purified by silica gel column chromatography (eluent 1% MeOH in EtOAc)
  2. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-92aa20dab29647828b49da118935553a
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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