Hydrochloric Acid → (+/-)-3-Benzoyl-4-((2-amino-2-ethylhexyl)thio)-1H-pyrrole

HRID 398825Notes

Reaction equation

HRID 398825 reaction equation
[C:1]([C:9]1[C:13]([S:14]C(=O)C2C=CC=CC=2)=[CH:12][N:11]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[CH2:36]([C:40]1([CH2:43][CH3:44])[CH2:42][NH:41]1)[CH2:37][CH2:38][CH3:39]>C(OCC)(=O)C.CO>[C:1]([C:9]1[C:13]([S:14][CH2:42][C:40]([NH2:41])([CH2:43][CH3:44])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:12][NH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 189688783-Benzoyl-4-(benzoylthio)-1-(triisopropylsilyl)pyrroleHCID 217099702-Butyl-2-ethylaziridine

Product 1

HCID 18968880(+/-)-3-Benzoyl-4-((2-amino-2-ethylhexyl)thio)-1H-pyrroleYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from step (c) (24.9 g), 250 ml methanol and 106 ml 1N sodium hydroxide was warmed to reflux for 10 minutes then 1N hydrochloric acid (53 ml) was added followed by 2-butyl-2-ethylaziridine (7.7 g, Synthetic Example 1(f)). After one hour the reaction was diluted with ethyl acetate and washed with 1N sodium hydroxide and then water. The organic layer was dried, filtered and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate-ethanol (3:1) to give a tan viscous oil (15.32 g). 1H NMR is consistent with proposed structure.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux for 10 minutes
  3. washwashed with 1N sodium hydroxide
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate-ethanol (3:1)

Sources & evidence

ORD record
ord-2066aeb38abe4dcd929312d9f9aefe20
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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