Acetic Anhydride → HCID 11947800, compound

HRID 2378365Notes

Reaction equation

HRID 2378365 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]1[C:18]2[O:17][C@@H:16](NC)[CH2:15][C:14]=2[CH:13]=[C:12]([F:21])[CH:11]=1.[CH:22]([N:25]([CH:28](C)C)CC)(C)[CH3:23].C(OC(=O)C)(=[O:33])C>C(Cl)Cl>[Cl:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[C:4]=1[C:10]1[C:18]2[O:17][C@@H:16]([CH2:28][NH:25][C:22](=[O:33])[CH3:23])[CH2:15][C:14]=2[CH:13]=[C:12]([F:21])[CH:11]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69257694HCID 69257694, compound

Product 1

HCID 11947800HCID 11947800, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-[7-(2,6-Dichloro-phenyl)-5-fluoro-2,3-dihydro-benzofuran-2-yl]-methylamine hydrochloride (0.050 g, 0.14 mmol) was suspended in 5.0 mL of methylene chloride and diisopropylethylamine (0.072 g, 0.56 mmol) and acetic anhydride (0.029 g, 0.28 mmol) added. The mixture was stirred at room temperature for 30 min, diluted to 100 mL with methylene chloride, washed with 50 mL portions of 2 N HCl (aqueous), saturated aqueous sodium bicarbonate and saturated brine. The solution was dried over sodium sulfate, filtered and concentrated in vacuum to give 0.043 g of the title compound as a white crystalline solid. 1H-NMR (CDCl3): multiplet 7.4 δ (1H); multiplet 7.33 δ (2H); doublet 6.95 δ (1H); doublet 6.72 δ (1H); broad singlet 5.8 δ (1H); multiplet 4.9 δ (1H); doublet of doublets 3.6 δ (1H); doublet of doublets 3.47 δ (1H); doublet of doublets 3.38 δ (1H); doublet of doublets 3.0 δ (1H); singlet 1.9 δ (3H).

Workup

  1. washwashed with 50 mL portions of 2 N HCl (aqueous), saturated aqueous sodium bicarbonate and saturated brine
  2. dry with materialThe solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-06dc443cfe5446528095f1023b98983e
Source dataset
uspto-grants-2008_12
Patent number
US07470799B2

Reaction notes

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