Tetrabutylammonium Fluoride → HCID 68548526, compound

HRID 1446064Notes

Reaction equation

HRID 1446064 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][C@@H:24]2[CH2:29][O:28][C:27]3=[N:30][C:31]([N+:33]([O-:35])=[O:34])=[CH:32][N:26]3[CH2:25]2)=[CH:18][CH:17]=1.C([SiH2]OC(C)(C)[C@@H]1OC(=O)N(C2C=CC(C3C=CC(CO[C@@H]4COC5=NC([N+]([O-])=O)=CN5C4)=CC=3)=C(F)C=2)C1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:17]=[CH:18][C:19]([CH2:22][O:23][C@H:24]2[CH2:29][O:28][C:27]3=[N:30][C:31]([N+:33]([O-:35])=[O:34])=[CH:32][N:26]3[CH2:25]2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57955501HCID 57955501, compoundHCID 131727898HCID 131727898, compound

Product 1

HCID 68548526HCID 68548526, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[2-Fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxymethyl)-biphenyl-4-yl]-5(R)-hydroxymethyl-oxazolidin-2-one. To a solution of 5(R)-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxymethyl)-biphenyl-4-yl]-oxazolidin-2-one (70 mg, 0.117 mmol) in THF (8.0 mL) was added TBAF (1.0 mL, 1.0 mmol, 1.0 M in THF). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, washed with brine, purified by flash chromatography to give the title product (36 mg, 64%) as a yellow solid. ESI MS m/z 485.3 (M+H+); 1H NMR (400 MHz, DMSO) δ 8.03 (s, 1H), 7.60 (dd, J=13.6, 2.4 Hz, 1H), 7.56-7.50 (m, 3H), 7.44-7.38 (m, 3H), 5.23 (t, J=5.6 Hz, 1H), 4.74-4.66 (m, 4H), 4.46 (d, J=12.0 Hz, 1H), 4.26-4.20 (m, 2H), 4.10 (t, J=9.2 Hz, 1H), 3.85 (dd, J=8.8, 6.0 Hz, 1H), 3.68-3.64 (m, 1H), 3.58-3.52 (m, 1H).

Workup

  1. washwashed with brine
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6123e575d5b64e519e9d17d627619f7f
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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