Hydrochloric Acid → tert-Butyl 4-(2-{(2-methoxyacetoxy)-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 252400Notes

Reaction equation

HRID 252400 reaction equation
[OH:1][CH:2]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([CH3:31])[CH:26]=[C:25]2[CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:3]([CH:19]([CH3:21])[CH3:20])[CH2:4][CH:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].N1C=CC=CC=1.[CH3:43][O:44][CH2:45][C:46](Cl)=[O:47].Cl>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:43][O:44][CH2:45][C:46]([O:1][CH:2]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([CH3:31])[CH:26]=[C:25]2[CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:3]([CH:19]([CH3:21])[CH3:20])[CH2:4][CH:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:47]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 66888806tert-butyl 4-(2-{hydroxy-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 66887418tert-Butyl 4-(2-{(2-methoxyacetoxy)-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.48 g of tert-butyl 4-(2-{hydroxy-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (diastereomer mixture) in 70 ml of toluene is admixed at 0° C. successively with 1.04 ml of pyridine, 1.11 ml of methoxyacetyl chloride and 0.62 g of 4-dimethylaminopyridine. The reaction mixture is stirred at 0° C. over 3.5 hours. The resulting mixture is poured onto 0.1N HCl (cold) and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water, 1M sodium hydrogencarbonate solution and brine, dried over sodium sulphate and filtered, and the filtrate is concentrated by evaporation. The title compound (diastereomer mixture) is obtained as a white foam from the residue by means of flash chromatography (SiO2 60F). Rf=0.32 (1:1 EtOAc-heptane). Rt=26.14 (gradient II).

Workup

  1. extractionextracted with tert-butyl methyl ether (2×)
  2. washThe combined organic phases are washed successively with water, 1M sodium hydrogencarbonate solution and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-26d1b29168244f3a83735b9163ee5e85
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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