Ethyl Acetate → HCID 178437010, compound

HRID 1892052Notes

Reaction equation

HRID 1892052 reaction equation
[CH3:1]C(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-].[C:13]([SiH2:17][O:18][C:19]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:20]([NH:24][C:25](=[O:42])[CH:26]([O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[CH:35][C:34]([C:40]#[CH:41])=[CH:33]2)[S:27][CH3:28])([CH3:23])[CH:21]=O)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO.[Cl-].[Na+].O>[C:13]([SiH2:17][O:18][C:19]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:20]([NH:24][C:25](=[O:42])[CH:26]([O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[CH:35][C:34]([C:40]#[CH:41])=[CH:33]2)[S:27][CH3:28])([CH3:23])[C:21]#[CH:1])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonateHCID 178437011HCID 178437011, compound

Product 1

HCID 178437010HCID 178437010, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dimethyl-1-diazo-2-oxopropylphosphonate (0.86 g) in dry methanol (20 ml) was added at R.T. to a solution of crude N-[1-(tert-Butyl-diphenyl-silanyloxymethyl)-1-methyl-2-oxo-ethyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide in dry methanol (40 ml). The reaction medium was cooled down to 0° C. and Potassium carbonate (0.773 g) was added portion wise along with additional dry methanol (10 ml). The reaction mixture was allowed to warm up to R.T., further stirred for 16 hrs and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure 1.84 g of crude mixture were isolated as a dark orange oil. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate) to give 1.523 g of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-prop-2-ynyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a yellow oil.

Workup

  1. temperatureto warm up to R.T.
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted thrice with ethyl acetate
  4. washwashed once with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration and concentration under reduced pressure 1.84 g of crude mixture
  7. customwere isolated as a dark orange oil
  8. customThe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c383596a092248929738917a89a1a909
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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