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Hydrochloric Acid → 1(R)-(3-Chloro-phenyl)-2-[1,1-dimethyl-2-(4-nitro-phenyl)-ethylamino]-ethanol

HRID 495711
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HRID 495711 반응식
[NH2:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.C[Si](C)(C)NC(=O)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C@H:27]1[O:29][CH2:28]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O.CO>[Cl:23][C:24]1[CH:25]=[C:26]([C@@H:27]([OH:29])[CH2:28][NH:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]2[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[CH:30]=[CH:31][CH:32]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 25989Acetamide, N-(trimethylsilyl)-HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 138976422-Methyl-1-(4-nitrophenyl)propan-2-amine

생성물 1

HCID 208268551(R)-(3-Chloro-phenyl)-2-[1,1-dimethyl-2-(4-nitro-phenyl)-ethylamino]-ethanol
수율 108.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매

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온도
95 °C

실험 절차

A solution of 2.2 g of 2-amino-2-methyl-1-(4-nitrophenyl)propane (prepared by the procedures described in J. Milecki, et al. J. Med. Chem., 30, 1563 (1987)) and N-trimethylsilylacetamide (1.6 g) in 2.2 mL DMSO was stirred for 30 min, then (R)-3-chlorostyrene oxide (1.8 g) was added and the resulting solution was stirred at 95° C. for 22 h. The reaction solution was allowed to cool, poured over a mixture of ice (30 g) and 6 N aqueous hydrochloric acid (10 mL). A small portion of MeOH was added to produce a homogenous solution, which was stirred for 30 min. The resulting solution was basified with saturated aqueous sodium carbonate, extracted with ethyl acetate, the organic phase dried (Na2SO4) and concentrated in vacuo to afford 4.3 g of the title compound (I-1a) as an orange oil.

후처리

  1. temperatureto cool
  2. customto produce a homogenous solution, which
  3. stirringwas stirred for 30 min
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phase dried (Na2SO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-16f1c4c9be71468b86d595aa474f30fa
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06939867B2

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