Pyridine → HCID 118086186, compound

HRID 1051560Notes

Reaction equation

HRID 1051560 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][O:10][CH3:11])[C:3]=1[CH2:12][CH2:13][C@H:14]([OH:16])[CH3:15].N1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[OH:16][C@H:14]([CH3:15])[CH2:13][CH2:12][C:3]1[C:4]([O:8][CH2:9][O:10][CH3:11])=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 118076092HCID 118076092, compound

Product 1

HCID 118086186HCID 118086186, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude (R)-4-(2-amino-6-(methoxymethoxy)phenyl)butan-2-ol (2.60 g, 11.54 mmol) and pyridine (2.80 mL, 34.6 mmol) in dichloromethane (52 mL) was cooled to 0° C. and treated with acetic anhydride (1.14 mL, 12.1 mmol). The ice bath was removed and the reaction mixture stirred at room temperature. After 45 min, the solution was washed with 5% aqueous sodium chloride solution (2×20 mL) and then concentrated under reduced pressure. Toluene (ca. 100 mL) was added and the mixture was concentrated. The residue was purified by column chromatography on silica gel (gradient elution with 25-100% ethyl acetate-hexanes) to afford (R)—N-(2-(3-hydroxybutyl)-3-(methoxymethoxy)phenyl)acetamide (2.7 g, 88%) as a pale yellow syrup. MS (ESI, pos. ion) m/z 290 [M+23]+.

Workup

  1. customThe ice bath was removed
  2. washthe solution was washed with 5% aqueous sodium chloride solution (2×20 mL)
  3. concentrationconcentrated under reduced pressure
  4. additionToluene (ca. 100 mL) was added
  5. concentrationthe mixture was concentrated
  6. customThe residue was purified by column chromatography on silica gel (gradient elution with 25-100% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-1c4d380a03ad4159b0dfb06549a2a5c0
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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