p-Toluenesulfonic acid → HCID 86601657, compound

HRID 503679Notes

Reaction equation

HRID 503679 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:32][CH2:33][O:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:25]1[CH2:29][O:28]C(C)(C)[O:26]1)=[O:22])(=[O:4])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:38][S:35]([O:34][CH2:33][CH2:32][N:8]([CH2:7][CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:25]([OH:26])[CH2:29][OH:28])=[O:22])(=[O:36])=[O:37]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 118014282-(2-({[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]amino}carbonyl){2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate

Product 1

HCID 86601657HCID 86601657, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2-({[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]amino}carbonyl){2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate (13g) [Palmer et al., J. Med. Chem. 1997, 40, 1272] (5.0 mmol) in MeOH (200 mL) was treated with p-toluenesulfonic acid (0.2 g) at room temperature for 4 h. Most of the MeOH was then evaporated, and the residue was taken up in EtOAc (200 mL), washed with satd. NaHCO3 and brine, dried and concentrated. Chromatography of the product on silica gel, eluting with EtOAc/MeOH (20:1), gave 2-(2-{[(2,3-dihydroxypropyl)amino]carbonyl}{2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate (13f) (2.0 g, 73%): as yellow foam;

Workup

  1. customMost of the MeOH was then evaporated
  2. washwashed with satd
  3. dry with materialNaHCO3 and brine, dried
  4. concentrationconcentrated
  5. washChromatography of the product on silica gel, eluting with EtOAc/MeOH (20:1)

Sources & evidence

ORD record
ord-5e2489af56df4112bfc9efe5111f8a7f
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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