Methanol → HCID 86614810, compound

HRID 2354119Notes

Reaction equation

HRID 2354119 reaction equation
[CH3:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([O-:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([O-:23])(=[O:22])=[O:21])[CH:8]=2)[N:3]=1.[Na+].[Na+].[CH2:26](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:27].C1S(=O)(=O)CCC1.CO>CCOC(C)=O>[CH2:26]([N+:3]1[C:4]2[C:9](=[CH:8][C:7]([S:20]([O-:23])(=[O:21])=[O:22])=[CH:6][CH:5]=2)[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])[C:2]=1[CH3:1])[CH3:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 6638Ethyl p-methylbenzenesulfonateHCID 31347SulfolaneHCID 86614812HCID 86614812, compound

Product 1

HCID 86614810HCID 86614810, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Disodium 2,3-dimethyl-3-(4-sulphonatobutyl)-3H-indole-5-sulphonate (1 g), ethyl-p-toluene sulphonate (0.95 ml; 5.56 mmol) and tetramethylenesulphone (10 ml) were heated together at 140° C. for 12 hrs. TLC (silica; 2:1 MeOH; EtOAc) showed the formation of a new product spot (rf=0.8), which turned magenta on standing. The product was precipitated into ethyl acetate and then filtered off and dried in vacuo to give the crude product as a dark purple solid; 1.5 g. The product was purified in multiple shots by HPLC (Vydac protein & peptide C18 (250 mm×25 mm); flow rate 10 ml/min; gradient of 0 to 25% B over 30 mins; eluant A=0.1% TFA in water and eluant B=0.1% TFA in acetonitrile; detection at 220 nm). The fractions containing the desired product were pooled and the solvent removed under reduced pressure. The product was obtained as a pale pink oil (400 mg).

Workup

  1. customThe product was precipitated into ethyl acetate
  2. filtrationfiltered off
  3. customdried in vacuo
  4. customto give the crude product as a dark purple solid
  5. customThe product was purified in multiple shots by HPLC (Vydac protein & peptide C18 (250 mm×25 mm); flow rate 10 ml/min; gradient of 0 to 25% B over 30 mins; eluant A=0.1% TFA in water and eluant B=0.1% TFA in acetonitrile; detection at 220 nm)
  6. additionThe fractions containing the desired product
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0cfdbd2aef8a4d148eecbc3b8ad77777
Source dataset
uspto-grants-2010_07
Patent number
US07750163B2

Reaction notes

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