4-Hydrazinobenzenesulfonic acid → 6-(2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

HRID 1667358

Reaction equation

HRID 1667358 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)N.[CH3:13][CH:14]([C:23](=O)[CH3:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>C(O)(=O)C>[CH3:24][C:23]1[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:13])[C:8]2[C:3](=[CH:4][CH:5]=[C:6]([S:9]([OH:12])(=[O:11])=[O:10])[CH:7]=2)[N:1]=1

Participants

4

Reactant 2

HCID 668254-Hydrazinobenzenesulfonic acidHCID 222668237-Methyl-8-oxononanoic acid

Product 1

HCID 598554226-(2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Hydrazinobenzenesulfonic acid (1.88 g, 10 mmol), 7-methyl-8-oxononanoic acid (2.8 g, 15 mmol) and glacial acetic acid (10 ml) were mixed and heated under reflux for 6 hrs. The solvent was then evaporated under vacuum and the residue triturated with diethyl ether until a solid was obtained. This was dried under vacuum to give crude product, 3.4 g (100%). This was purified by preparative HPLC as required (RPC18. Water+0.1% TFA→MeCN+0.1% TFA gradient). UV/Vis (Water+0.1% TFA): 274, 229, 204 nm. 1H-nmr (D2O) δ 0.6-0.9 (2H, broad m), 1.10-1.25 (2H, broad m), 1.35-1.50 (2H, m), 1.60 (3H, s), 2.10-2.40 (2H, broad m+2H, t), 7.77 (1H, d), 7.97 (1H, dd) and 8.06 (1H, d)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hrs
  3. customThe solvent was then evaporated under vacuum
  4. customthe residue triturated with diethyl ether until a solid
  5. customwas obtained
  6. customThis was dried under vacuum
  7. customto give crude product, 3.4 g (100%)
  8. customThis was purified by preparative HPLC

Sources & evidence

ORD record
ord-686d6b4543cf441880c75b51e59452c7
Source dataset
uspto-grants-2011_10
Patent number
US08044203B2

Linked notes

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