p-Toluenesulfonic acid → HCID 69600972, compound

HRID 2215088Notes

Reaction equation

HRID 2215088 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C@@H:5]([CH2:15][O:16]C2CCCCO2)[CH2:4][S:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CCO>[OH:16][CH2:15][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]#[N:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 69601148HCID 69601148, compound

Product 1

HCID 69600972HCID 69600972, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-1 (0.97 g, 3.0 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 50–80% EtOAc/hexanes to yield 0.65 g of 4-2 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.92–3.73 (m, 3H), 3.68–3.60 (m, 1H), 3.42 (dd, 1H), 3.28 (dd, 1H), 3.10 (m, 1H), 2.37(t, 2H), 1.71–1.46 (m, 6H), 1.39–1.33 (m, 2H); MS (+ESI): m/z 243.1 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-6ec3c79fb50d4fe089e24f14dc468379
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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