Tributylphosphine → Methyl 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoate

HRID 2177787Notes

Reaction equation

HRID 2177787 reaction equation
[CH2:1](P(CCCC)CCCC)CCC.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:28]1([S:34]([CH2:37][C:38]2[C:43]([C:44]([OH:46])=[O:45])=[C:42]([OH:47])[C:41]([C:48]3[CH:52]=[CH:51][O:50][CH:49]=3)=[CH:40][CH:39]=2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O[CH2:54][CH2:55][N:56]([CH3:64])[C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60]>C1COCC1.O.C(OCC)(=O)C>[C:28]1([S:34]([CH2:37][C:38]2[C:43]([C:44]([O:46][CH3:1])=[O:45])=[C:42]([O:47][CH2:54][CH2:55][N:56]([C:57]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:63])[CH3:64])[C:41]([C:48]3[CH:52]=[CH:51][O:50][CH:49]=3)=[CH:40][CH:39]=2)(=[O:36])=[O:35])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 52914186HCID 52914186, compound2×

Product 1

HCID 67107624Methyl 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoateYield 73.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Tri-n-butylphosphine (0.054 g) was added dropwise to a cooled solution of di-isopropyl azodicarboxylate (0.065 g) in dry THF (1 ml) at 0° C. The resultant solution was warmed to room temperature for 10 minutes then re-cooled to 0° C. A mixture of methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (Intermediate 114, 0.05 g) and t-butyl N-(2-hydroxyethyl)-N-methylcarbamate (0.025 g) in THF (1 ml) was added dropwise and the reaction mixture was warmed to room temperature and stirred for 3 hours. Ethyl acetate and water were added and the organic layer was dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (1:3) to give methyl 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoate (0.054 g) as a gum.

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction mixture was warmed to room temperature
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane (1:3)

Sources & evidence

ORD record
ord-a359b8597c524b1484700a236fa72326
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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