1-Propanol → HCID 23446846, compound

HRID 1841647Notes

Reaction equation

HRID 1841647 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11](OS(C)(=O)=O)[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:38]([OH:41])[CH2:39][CH3:40]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:41][CH2:38][CH2:39][CH3:40])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 8471TriethylamineHCID 23446837HCID 23446837, compound

Product 1

HCID 23446846HCID 23446846, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-(4-chloro-phenyl)-N-mesyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (452 mg, 1 mmol) in a mixture of 6 ml acetonitrile and 6 ml n-propanol during a period of 12 hours a solution of triethylamine (0.146 ml, 1.05 mmol) in 12 ml of acetonitrile is added dropwise. The mixture is stirred for 20 hours at room temperature. The solvent and excess n-propanol is removed under reduced pressure and the residue was diluted with ethyl acetate (30 ml), washed with water, 1N HCl, and brine, and dried with Na2SO4. After evaporation of the solvent the product is purified by flash chromatography (ethyl acetate:hexane, 1:2) to yield 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy-acetamide in form of an oil. 1H-NMR (300 MHz, CDCl3): 0.89(t, 3H, CH3), 1.58(q, 2H, CH2), 2.50(t, 1H, C≡CH), 2.79(t, 2H, CH2CH2), 3.35(t, 2H, OCH2), 3.52(dt, 2H, CH2CH2), 3.83(s, 3H, OCH3), 4.63(s, 1H, CHOH), 4.74(d, 2H, OCH2), 6.67-7.30(m, 8H, CH arom., NH).

Workup

  1. additionis added dropwise
  2. customThe solvent and excess n-propanol is removed under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (30 ml)
  4. washwashed with water, 1N HCl, and brine
  5. dry with materialdried with Na2SO4
  6. customAfter evaporation of the solvent the product
  7. customis purified by flash chromatography (ethyl acetate:hexane, 1:2)

Sources & evidence

ORD record
ord-03cd42e820ca48a5a00b92b07181fe93
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

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