Methyl 4-bromobutyrate → HCID 69003979, compound

HRID 750026Notes

Reaction equation

HRID 750026 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][CH:22]=[N:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.[CH3:26][O:27][C:28](=[O:33])[CH2:29][CH2:30][CH2:31]Br>ClCCl.C(N(CC)CC)C>[CH3:26][O:27][C:28](=[O:33])[CH2:29][CH2:30][CH2:31][N:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][CH:22]=[N:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 107604Methyl 4-bromobutyrateHCID 69001469HCID 69001469, compound

Product 1

HCID 69003979HCID 69003979, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of (5-{4-[4-((R)-1-pyrrolidin-2-ylmethoxy)-phenoxy]-phenyl}-oxazole (150 mg, 0.4 mmol) in anhydrous dichloromethane (0.5mL) was added methyl-4-bromobutyrate (80 mg, 0.44 mmol) in dichloromethane (0.5 mL) and triethylamine (81 mg, 0.8 mmol. The resulting mixture was purged with nitrogen and stirred at rt for 16 h. dichloromethane was removed in vacuo and crude mixture was partioned between EtOAc and water. EtOAc layer was removed, washed with brine, dried over anhydrous MgSO4 and concentrated. The crude mixture was purified by silica gel flash chromatography 3 (40% EtOAc/hexane) to obtain the title product as yellow oil (95 mg, 55%).

Workup

  1. customThe resulting mixture was purged with nitrogen
  2. customwas removed in vacuo and crude mixture
  3. customEtOAc layer was removed
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel flash chromatography 3 (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-a3b49a4b6ed94959824eeed74d04a994
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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