HCID 21051177, compound → HCID 9802054, compound

HRID 2213373Notes

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]=[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.C1(C(C2C=CC=CC=2)CCO[C:41](=[S:45])[CH:42]([F:44])[F:43])C=CC=CC=1>>[F:21][C:19]1[CH:20]=[C:15]([N:11]2[CH2:10][CH:9]([CH2:8][NH:7][C:41](=[S:45])[CH:42]([F:44])[F:43])[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 21051177HCID 21051177, compound

HCID 21874093HCID 21874093, compound

Product 1

HCID 9802054HCID 9802054, compound

Procedure

The title compound 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 (250 mg, 0.59 mmol) and difluorothioacetic acid-O-(3,3-diphenyl-propyl) ester (420 mg, 1.25 mmol) following the method described for Example 10. The crude product is purified by silica gel column chromatography (gradient 50 to 100% EtOAc in hexanes). MS (m/z): 418 [M+1]+. 1H NMR (300 MHz, CDCl3) δ11.13 (br. s, 1H), 7.46–7.38 (m, 3H), 6.49 (t, J=55.2 Hz, 1H), 5.07–4.98 (m, 2H), 4.19 (t, J=9.1 Hz), 1H), 4.02–3.76 (m, 5H).

Workup

customThe crude product is purified by silica gel column chromatography (gradient 50 to 100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-189bfb8b77fb4474b3e2a603937aa4b6
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105547B2

Reaction notes

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