Ethyl Glycolate → HCID 59146110, compound

HRID 1512808Notes

Reaction equation

HRID 1512808 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].CC1C=CC(S(O[CH2:21][CH2:22][CH2:23][C:24]2[C:32]3[C:27](=[C:28]([C:33]4[N:37]=[C:36]([C:38]5[CH:43]=[CH:42][C:41]([O:44][CH:45]([CH3:47])[CH3:46])=[C:40]([Cl:48])[CH:39]=5)[O:35][N:34]=4)[CH:29]=[CH:30][CH:31]=3)[N:26]([CH3:49])[CH:25]=2)(=O)=O)=CC=1>CN(C=O)C>[Cl:48][C:40]1[CH:39]=[C:38]([C:36]2[O:35][N:34]=[C:33]([C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[C:27]=3[N:26]([CH3:49])[CH:25]=[C:24]4[CH2:23][CH2:22][CH2:21][O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:37]=2)[CH:43]=[CH:42][C:41]=1[O:44][CH:45]([CH3:46])[CH3:47]

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 59146074HCID 59146074, compound

Product 1

HCID 59146110HCID 59146110, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of ethyl hydroxyacetate (90 mg) in DMF (4 mL) at 20° C. was added NaH (69 mg), the mixture was stirred for 15 mins. Then a solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propyl 4-methylbenzenesulfonate (D129) (100 mg) in DMF (4 mL) was added dropwise during 1 min. The reaction was stirred at 20° C. for 48 h. The reaction mixture was quenched with water, partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was washed with water and brine, dried over sodium sulphate and evaporated to give the crude product ethyl ({3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propyl}oxy)acetate (D105) (80 mg). MS (ES): C27H30ClN3O5 requires 511; found 512.2 (M+H+).

Workup

  1. stirringThe reaction was stirred at 20° C. for 48 h
  2. customThe reaction mixture was quenched with water
  3. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-e69872f56f2a4f49b34ed11d3b332e24
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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