p-Toluenesulfonic acid monohydrate → HCID 59758847, compound

HRID 914364Notes

Reaction equation

HRID 914364 reaction equation
[C:1]([O:5][C:6](=[O:42])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34]C(OC(C)(C)C)=O)=[CH:30][CH:29]=2)[C:19]2[N:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][N:20]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:42])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=2)[C:19]2[N:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][N:20]=2)[N:15]=1)([CH3:8])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59759009HCID 59759009, compound

Product 1

HCID 59758847HCID 59758847, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-[(4-{2-[{4-[(tert-Butoxycarbonyl)amino]benzyl}(5-ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (1.2 g) synthesized in Example 439-1 was dissolved in dichloromethane (20 mL), p-toluenesulfonic acid monohydrate (3.64 g) was added thereto by small portions at room temperature. After 2.5 hr, the mixture was diluted with dichloromethane, washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 1:1) to give the title compound (0.78 g) as a colorless oil.

Workup

  1. customat room temperature
  2. washwashed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-357bc5c3aa1245baa78526bc6c0eb919
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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