p-Toluenesulfonic acid → HCID 69601136, compound

HRID 2215083Notes

Reaction equation

HRID 2215083 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@@H:5]([CH2:18][O:19]C2CCCCO2)[CH2:4][S:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CCO>[OH:19][CH2:18][C@H:5]1[CH2:4][S:3][C:2](=[O:1])[N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 69601020HCID 69601020, compound

Product 1

HCID 69601136HCID 69601136, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-5 (0.5 g, 2.3 mmol) in 10 mL EtOH was added p-toluene sulfonic acid (50 mg) and the resulting solution was stirred overnight at room temperature Triethylamine (0.1 mL) was added and the solution was concentrated in vacuo. The compound was purified by flash chromatography using 80% EtOAc/hexanes to yield 0.4 g of 3-6 as a colorless oil. 1H NMR (400 MHz, acetone-d6): □ 4.2 (t, 1H), 4.1 (q, 3H), 3.9 (m, 1H), 3.7 (m, 2H), 3.6 (m, 1H), 3.4 (dd, 1H), 3.3 (dd, 1H), 3.1 (m, 1H), 2.3 (t, 2H), 1.3–1.7 (m, 8H), 1.2 (t, 2H).

Workup

  1. additionwas added
  2. concentrationthe solution was concentrated in vacuo
  3. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-be44e87d92b04e2c8d753da7d2cfe8d0
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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