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

HRID 243799

Reaction equation

HRID 243799 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4716a21cec964f60bcbd9ed83bc69b56
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Linked notes

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