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

HRID 398825ノート

反応式

HRID 398825 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2066aeb38abe4dcd929312d9f9aefe20
出典データセット
uspto-grants-1998_10
特許番号
US05817652

反応ノート

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