Tetrahydrofuran → HCID 59488932, compound

HRID 2207457Notes

Reaction equation

HRID 2207457 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[C:18]([Si](C)(C)C)[N:17]=[N:16]3)[O:11][C:10]2=[O:24])[CH:6]=[CH:5][C:4]=1[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][CH2:33][C:34]2[N:35]=[N:36][N:37]([CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH:38]=2)=[CH:27][CH:26]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(O)(=O)C>[F:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:24])[CH:6]=[CH:5][C:4]=1[C:25]1[CH:26]=[CH:27][C:28]([CH2:31][NH:32][CH2:33][C:34]2[N:35]=[N:36][N:37]([CH2:39][C:40]3[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[CH:38]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 66884061HCID 66884061, compound

Product 1

HCID 59488932HCID 59488932, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[2-Fluoro-4′-({[1-(4-methoxy-benzyl)-1H-[1,2,3]triazol-4-ylmethyl]-amino}-methyl)-biphenyl-4-yl]-5-(4-trimethylsilanyl-[1,2,3]triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (SC-167-63-2, 0.22 g, 0.343 mmol) in an 1 M solution of tetrabutylammonium fluoride in THF (TBAF, 1.4 mL, 1.4 mmol, 4.0 equiv) was treated with acetic acid (HOAc, 5.0 mL) at room temperature, and the resulting reaction mixture was stirred at room temperature for 24 h. When TLC and HPLC/MS showed that the reaction was complete, the solvents were removed in vacuo. The residue was treated with H2O (30 mL) at room temperature and the resulting mixture was stirred at room temperature for 1 h. The solids were collected by filtration, washed with H2O (2×10 mL) and 20% EtOAc/hexane (2×20 mL), dried in vacuo. The crude, desired (5R)-3-[2-Fluoro-4′-({[1-(4-methoxy-benzyl)-1H-[1,2,3]triazol-4-ylmethyl]-amino}-methyl)-biphenyl-4-yl]-5-[1,2,3]triazol-1-ylmethyl-oxazolidin-2-one (SC-167-71, 0.17 g, 0.195 g theoretical, 87%) was obtained as off-white powders, which by HPLC/MS and 1H NMR was found to be essentially pure and was directly used in the subsequent reactions without further purification. For SC-167-71: 1H NMR (300 MHz, DMSO-d6) 3.73 and 3.75 (two, s, 4H), 3.94-3.97 (m, 1H, 4.29 (t, 1H), 4.85 and 4.87 (dd, 2H), 5.15-5.20 (m, 1H, 5.48 (s, 1H), 6.91 and 6.94 (d, 2H), 7.28-7.58 (m, 10H, aromatic-H), 7.78 (s, 11-1, triazole-H), 7.98 (s, 1H, triazole-H), 8.19 (s, 1H, triazole-H); C30H29FN8O3, LCMS (EI) m/e 568 (M++H).

Workup

  1. customthe resulting reaction mixture
  2. customthe solvents were removed in vacuo
  3. additionThe residue was treated with H2O (30 mL) at room temperature
  4. stirringthe resulting mixture was stirred at room temperature for 1 h
  5. filtrationThe solids were collected by filtration
  6. washwashed with H2O (2×10 mL) and 20% EtOAc/hexane (2×20 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b72daf0c7f7a4e70a31b74864720265e
Source dataset
uspto-grants-2016_06
Patent number
US09376400B2

Reaction notes

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