2-Bromoethanol → 2-{5-[4-(4-{2-[2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-tetrazol-1-yl}-ethanol

HRID 1768059Notes

Reaction equation

HRID 1768059 reaction equation
[H-].[Na+].[F:3][S:4]([F:38])([F:37])([F:36])([F:35])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[O:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]4[N:31]=[N:32][NH:33][N:34]=4)=[CH:22][CH:21]=3)[N:17]=2)=[CH:7][CH:6]=1.Br[CH2:40][CH2:41][OH:42]>CN(C=O)C>[F:38][S:4]([F:35])([F:3])([F:36])([F:37])[C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH:12][C:13]2[O:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]4[N:31]=[N:32][N:33]([CH2:40][CH2:41][OH:42])[N:34]=4)=[CH:24][CH:25]=3)[N:17]=2)=[CH:9][CH:10]=1.[F:38][S:4]([F:35])([F:3])([F:36])([F:37])[C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH:12][C:13]2[O:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]4[N:34]([CH2:40][CH2:41][OH:42])[N:33]=[N:32][N:31]=4)=[CH:24][CH:25]=3)[N:17]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 113299725-[4-(4-{2-[(E)-2-(-4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-2H-tetrazole

Product 2

HCID 729684352-{5-[4-(4-{2-[2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-tetrazol-1-yl}-ethanolHCID 729816372-{5-[4-(4-{2-[2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-tetrazol-2-yl}-ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.4 mg (0.16 mmol) 95% sodium hydride were added to a solution of 82.0 mg (0.156 mmol) 5-[4-(4-{2-[(E)-2-(-4-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-2H-tetrazole in 2.0 ml DMF and stirred for 15 min. 19.8 mg (0.159 mmol) 2-bromoethanol were added, the mixture stirred overnight and evaporated. Separation by LC-MS (methanol/water 3:1, pH=2.3) on a C4 reversed phase column gave 6 mg of the title compound and 32 mg of 2-{5-[4-(4-{2-[2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-tetrazol-1-yl}-ethanol (example 7).

Workup

  1. stirringthe mixture stirred overnight
  2. customevaporated
  3. customSeparation by LC-MS (methanol/water 3:1, pH=2.3) on a C4

Sources & evidence

ORD record
ord-99562eb8ec47494f979a6f4690fe8a48
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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