Diisopropylethylamine → 1-(5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenyl)-3-((1S,2R)-1-hydroxy-2,3-dihydro-1H-indene-2-yl)urea

HRID 243799

반응식

HRID 243799 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][C@@H:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:26]1[OH:34].C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12]([NH:24][C@@H:25]2[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C@@H:26]2[OH:34])=[O:19])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 444305L-Tartaric acidHCID 11008081rac-(1R,2S)-2-amino-2,3-dihydro-1H-inden-1-olHCID 681068792,2,2-Trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate

생성물 1

HCID 681078361-(5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenyl)-3-((1S,2R)-1-hydroxy-2,3-dihydro-1H-indene-2-yl)urea수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of 2,2,2-trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate (1.50 g, 3.90 mmol), (1S,2R)-2-amino-2,3-dihydro-1H-indene-1-ol.L-tartaric acid salt (1.28 g, 4.29 mmol) and N,N-diisopropylethylamine (2.37 mL, 13.6 mmol) in acetonitrile (19.5 mL) was heated to reflux. After 17 hours, the mixture was allowed to cool and the reaction solution was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/50-0/100) to obtain 1.09 g of the captioned compound (73% yield).

후처리

  1. temperatureto cool
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/50-0/100)

출처 및 근거

ORD 기록
ord-4716a21cec964f60bcbd9ed83bc69b56
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653304B2

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