Water → HCID 53904704, compound

HRID 1600986Notes

Reaction equation

HRID 1600986 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@H:16]([OH:25])[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.O.C(N(CC)CC)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>ClCCl>[C:34]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@H:16]([OH:25])[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 962Water2×HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54036729HCID 54036729, compound

Product 1

HCID 53904704HCID 53904704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2R)-1-(3'-Hydroxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol (0.34 g, Example 99) was dissolved in dichloromethane (10 ml) and cooled to 0° C. using ice and water. Triethylamine (0.14 ml) and acetic anhydride (0.09 ml) were added and the reaction mixture allowed to room temperature with stirring for 18 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (97:3) to give the title compound as an oil (0.20 g).

Workup

  1. customallowed to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (97:3)

Sources & evidence

ORD record
ord-48e2b5aba9794d7085f28b0b9e81ca02
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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