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

HRID 398825노트

반응식

HRID 398825 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2066aeb38abe4dcd929312d9f9aefe20
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817652

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