Tetrahydrofuran → HCID 19434459, compound

HRID 1735831Notes

Reaction equation

HRID 1735831 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([C:28]([O:30][CH3:31])=[O:29])[CH:17]=2)[C:9]([CH2:13][OH:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6].Br[C:33]1[S:34][CH:35]=[C:36](C)[C:37]=1[C:38]([O:40][CH3:41])=[O:39].[CH2:43]1COCC1>>[CH2:3]([C:7]1[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([C:28]([O:30][CH3:31])=[O:29])[CH:17]=2)[C:9]([CH2:13][O:14][CH2:43][C:33]2[S:34][CH:35]=[CH:36][C:37]=2[C:38]([O:40][CH3:41])=[O:39])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 19434468HCID 19434468, compoundHCID 676929251266396-99-9

Product 1

HCID 19434459HCID 19434459, compoundYield 62%

Conditions

Temperature
60 °C

Procedure

A suspension of 145 mg of 80% NaH in anhydrous THF heated to 60° C. is added with 1 g of 2-butyl-4-chloro-5-hydroxymethyl-1-[(2-methoxycarbonyl-1,1'-biphenyl-4-yl)methyl]-1H-imidazole dissolved in 8 ml of THF. The resulting solution is stirred at 60° C. for 1 h, cooled to 25° C. and 0.7 g of methyl 2-bromo-methylthien-3-yl-carboxylate are added dissolved in THF. After 1 hour the mixture is filtered and the solvent is evaporated off under reduced pressure. The crude product is purified by F.C. (eluent ethyl acetate/hexane 4:6). 0.84 g of a glassy oil are obtained (62% yield). 1H NMR (CDCl3), δ: 0.88 (t, 3 H); 1.35 (m, 2 H); 1.67 (m, 2 H); 2.61 (t, 2 H); 3.64 (s, 3 H); 3.83 (s, 3 H); 4.53 (s, 2 H); 5.00 (s, 2 H); 5.24 (s, 2 H); 7.02-7.87 (m, 10 H).

Workup

  1. temperaturecooled to 25° C.
  2. filtrationAfter 1 hour the mixture is filtered
  3. customthe solvent is evaporated off under reduced pressure
  4. customThe crude product is purified by F.C

Sources & evidence

ORD record
ord-0f39daf0991f4fda867a9001a6a1dfaf
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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