Ethanolamine → HCID 68778583, compound

HRID 2263557Notes

Reaction equation

HRID 2263557 reaction equation
COCC(O[CH:7]([C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:30]=[C:29]2[CH2:43][CH2:44][CH2:45][O:46][CH3:47])[CH:8]([CH2:12][CH:13]([N:23]=[N+]=[N-])[CH:14]1[CH2:18][CH:17]([CH:19]([CH3:21])[CH3:20])[C:16](=[O:22])[O:15]1)[CH:9]([CH3:11])[CH3:10])=O.C(CN)O>C(O)C.[Pd]>[NH2:23][CH:13]([CH:14]1[O:15][C:16](=[O:22])[CH:17]([CH:19]([CH3:21])[CH3:20])[CH2:18]1)[CH2:12][CH:8]([CH2:7][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:40])([CH3:42])[CH3:41])[CH:30]=[C:29]2[CH2:43][CH2:44][CH2:45][O:46][CH3:47])[CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 86624609HCID 86624609, compound

Product 1

HCID 68778583HCID 68778583, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The stirred solution of 1.86 g of 2-[2 azido-2-(4-isopropyl-5-oxotetrahydrofuran-2-yl)ethyl]-1-[3-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-indol-5-yl]-3-methylbutyl methoxyacetate (diastereomer mixture) in 100 ml of ethanol is hydrogenated at 0° C. in the presence of 0.165 ml of ethanolamine and 1.88 g of 10% Pd/C over 6 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The residue is admixed with 100 ml of 1M sodium hydrogencarbonate solution and extracted with tert-butyl methyl ether (3×). The combined organic phases are dried over sodium sulphate and filtered, and the filtrate is concentrated by evaporation. The crude title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60 F). Rt=24.2 (gradient II).

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. extractionextracted with tert-butyl methyl ether (3×)
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-8f500bc9630d4a54b2643941c8e5d194
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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