HCID 10730396, compound → HCID 88451558, compound

HRID 1109310Notes

Reaction equation

HRID 1109310 reaction equation
[OH:1][CH2:2][CH2:3][O:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=1.[CH2:20]([C:29](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>C(Cl)Cl.N1C=CC=CC=1>[CH2:20]([C:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:1][CH2:2][CH2:3][O:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:9][CH:8]=1)[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 10730396HCID 10730396, compoundHCID 14836583p-Anisyldiphenylmethyl chloride

Product 1

HCID 88451558HCID 88451558, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.8 grams (10.6 mmol) of N-(2-hydroxy-ethoxy)-4-pivaloylbenzamide in 5 ml of methylene chloride and 3 ml of pyridine at 0° C. are added 3.92 grams (12.7 mmol) of ρ-anisylchlorodiphenylmethane. The mixture is warmed to room temperature over two hours and then diluted with 40 ml of methylene chloride. This solution is washed with 50 ml of 10% sodium bicarbonate and 30 ml of brine, dried over magnesium sulfate and concentrated by evaporation. The residue is purified by column chromatography using 5:1 hexane/ethyl acetate as the eluent to obtain the protected product, N-(2-[ρ-anisyldiphenylmethyloxy]ethoxy)-4-pivaloylbenzamide.

Workup

  1. washThis solution is washed with 50 ml of 10% sodium bicarbonate and 30 ml of brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-437201af911d4e7f9519cf0cf8fb770d
Source dataset
uspto-grants-1994_06
Patent number
US05319123

Reaction notes

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