Ammonium Chloride → HCID 15063398, compound

HRID 475477Notes

Reaction equation

HRID 475477 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:17][CH2:18][C:19](OCC)=[O:20])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1COCC1>[O:20]=[C:19]1[CH:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])[N:8]2[C:16]3[C:11]([CH:10]=[C:9]2[CH2:17][CH2:18]1)=[CH:12][CH:13]=[CH:14][CH:15]=3

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15063397HCID 15063397, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15063398HCID 15063398, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-[1-(2-tert-butoxy-2-oxoethyl)-1H-indol-2-yl]propanoate from Step 4 in THF (0.06 M) at −10° C. was added 1 M potassium tert-butoxide (2.5 equiv.) dropwise. The reaction mixture was allowed to warm to rt over a period of 1 h. and then stirred at rt overnight. The reaction mixture was poured into aqueous ammonium chloride and extracted with excess EtOAc (2×). The combined organic layers were washed with brine, dried with MgSO4, filtered and concentrated under vacuum to afford the crude title compound (92%) as a dark oil. This material was used in the next step without further purification.

Workup

  1. extractionextracted with excess EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f328f2d2e7834fb3b1498e4096933c1f
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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