Acetic Anhydride → HCID 67777582, compound

HRID 1026359Notes

Reaction equation

HRID 1026359 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@@H:9]([CH3:29])[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([CH3:28])[CH2:22][C:21]3[CH:23]=[CH:24][C:25]([OH:27])=[CH:26][C:20]=3[O:19]2)=[N:16][CH:17]=1>N1C=CC=CC=1.CO.[OH-].[Na+]>[OH:27][C:25]1[CH:24]=[CH:23][C:21]2[CH2:22][C:18]([C:15]3[N:16]=[CH:17][C:12]([O:11][CH2:10][C@@H:9]([NH:8][C:1](=[O:3])[CH3:2])[CH3:29])=[CH:13][CH:14]=3)([CH3:28])[O:19][C:20]=2[CH:26]=1

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 67777689HCID 67777689, compound

Product 1

HCID 67777582HCID 67777582, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of acetic anhydride (0.126 mL) was added dropwise to a solution of diastereomer of 2-(5-{[(2S)-2-aminopropyl]oxy}pyridin-2-yl)-2-methyl-2,3-dihydro-1-benzofuran-6-ol (500 mg) in pyridine (15 mL) at ambient temperature. After being stirred at ambient temperature for 2 hr, the mixture was diluted with methanol (15 mL) and 4 M sodium hydroxide (10 mL). The mixture was stirred at ambient temperature for 15 hr. The organic solvent was removed under reduced pressure, and the aqueous solution was acidified with 4 M hydrochloric acid and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (350 mg).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 15 hr
  2. customThe organic solvent was removed under reduced pressure
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2a5aa607c43649c6ad8db878ddf4a8e3
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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