7-Methyl-8-oxononanoic acid → 6-(1,2-dimethyl-6,8-disulfo-1H-benzo[e]indol-1-yl)hexanoic acid

HRID 1435162Notes

Reaction equation

HRID 1435162 reaction equation
[Cl-].[S:2]([C:6]1[CH:15]=[C:14]([S:16]([OH:19])(=[O:18])=[O:17])[CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([NH2+:20]N)=[CH:11]2)([OH:5])(=[O:4])=[O:3].[CH3:22][CH:23]([C:32](=O)[CH3:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30]>C(O)(=O)C>[CH3:22][C:23]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:11]2[C:12]3[CH:13]=[C:14]([S:16]([OH:19])(=[O:18])=[O:17])[CH:15]=[C:6]([S:2]([OH:5])(=[O:4])=[O:3])[C:7]=3[CH:8]=[CH:9][C:10]=2[N:20]=[C:32]1[CH3:33]

Participants

4

Reactant 2

HCID 222668237-Methyl-8-oxononanoic acidHCID 86603524(5,7-Disulfo-2-naphthyl)hydrazinium chloride

Product 1

HCID 579377396-(1,2-dimethyl-6,8-disulfo-1H-benzo[e]indol-1-yl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(5,7-Disulfo-2-naphthyl)hydrazinium chloride (2.0 g), 7-methyl-8-oxononanoic acid (1.5 g) and acetic acid (15 ml) were heated from 80-140° C. for a total of 24 hrs. After evaporation of the solvent under vacuum, the residue was triturated with 2-propanol to give a pink solid. This solid was collected by filtration, washed with 2-propanol, then excess diethyl ether and dried under vacuum over phosphorus pentoxide. Yield of crude product=1.96 g. This was purified as required by preparative HPLC (RPC18. Water/MeCN/TFA) to give pure product. 1H-nmr (D2O) δ 0.25-0.4 (1H, broad m), 0.5-0.65 (1H, broad m), 1.00 (2H, m), 1.25 (2H, m), 1.78 (3H, s), 2.06 (2H, t), 2.35-2.5 (1H, broad m), 2.65-2.8 (1H, broad m), 2.90 (3H, s), 8.05 (1H, d), 8.58 (1H, d), 8.70 (1H, d) and (8.97 (1H, d). MS (LCMS) MH+470. Acc. Mass: MH+470.0931 (−2.6 ppm for C20H24NO8S2).

Workup

  1. customAfter evaporation of the solvent under vacuum
  2. customthe residue was triturated with 2-propanol
  3. customto give a pink solid
  4. filtrationThis solid was collected by filtration
  5. washwashed with 2-propanol
  6. dry with materialexcess diethyl ether and dried under vacuum over phosphorus pentoxide
  7. customThis was purified
  8. customto give pure product

Sources & evidence

ORD record
ord-450c90a354c546aebf3a325194fd7afb
Source dataset
uspto-grants-2009_11
Patent number
US07615646B2

Reaction notes

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