p-Toluenesulfonic acid → HCID 15229847, compound

HRID 1653665Notes

Reaction equation

HRID 1653665 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH:11]1[CH2:16][CH2:15][C:14]2([CH2:21][CH:20](O)[C:19]3[CH:23]=[C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[CH:26][C:18]=3[O:17]2)[CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+].CCOC(C)=O>C1(C)C=CC=CC=1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH:11]1[CH2:16][CH2:15][C:14]2([CH:21]=[CH:20][C:19]3[CH:23]=[C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH:25]=[CH:26][C:18]=3[O:17]2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 15229844HCID 15229844, compound

Product 1

HCID 15229847HCID 15229847, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of the alcohol from example 2 above (310 mg, 0.7 mmol) in toluene (8 ml )was added p-toluene sulfonic acid (200 mg). This was boiled without a condenser until the reaction mixture was a gum. It was then cooled to r.t., sat. NaHCO3 (1 00 ml ) and EtOAc (1 00 ml ) were added. The biphasic mixture was stirred at r.t until all of the gummy solid dissolved. The layers were separated and the organic phase was dried over Na2SO4 and evaporated under reduced pressure to give 166 mg of a pale yellow oil, 55.8%.1H NMR (CDCl3)δ7.28-6.79 (m, 7H), 6.30 (d, J=1OHz, 1H), 5.55 (d, J=10 Hz, 1H), 3.83 (s, 2H), 2.91 (s, 7H), 2.62-2.48 (m, 1H), 2.20 (d, J=12 Hz, 2H), 2.00-1.82 (m, 4H), 1.45 (dt, J=13 Hz, J=4 Hz, 2H).

Workup

  1. customThis was boiled without a condenser until the reaction mixture
  2. dissolutiondissolved
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f77acf15cb2749f8a9881d78d62def81
Source dataset
uspto-grants-1995_04
Patent number
US05403846

Reaction notes

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