Hydrochloric Acid → HCID 56961339, compound

HRID 1506894Notes

Reaction equation

HRID 1506894 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[N:12]([CH3:27])[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[C:19]=2[C:20]([O:22]C(C)(C)C)=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>O1CCOCC1>[C:1]1([S:7]([NH:10][C:11]2[N:12]([CH3:27])[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[C:19]=2[C:20]([OH:22])=[O:21])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68279012HCID 68279012, compound2×

Product 1

HCID 56961339HCID 56961339, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-benzenesulphonylamino-1-methyl-4,5,6,7-tetrahydro-1H-indole-3-carboxylate (Intermediate 21, 0.3 g) was added to HCl in dioxane (4M, 3.8 ml) at 0° C. The cold bath was removed and the mixture was allowed to warm to room temperature and then stirred for 2 hours. The mixture was cooled to 0° C. and neutralised with saturated aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate, washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with DCM (15 ml). The solid was collected by filtration and triturated with hot ethyl acetate (3 ml). The solid was collected by filtration and air dried to afford 2-benzenesulphonylamino-1-methyl-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (0.017 g) as a white solid.

Workup

  1. customThe cold bath was removed
  2. temperatureThe mixture was cooled to 0° C. and neutralised with saturated aqueous sodium bicarbonate solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was triturated with DCM (15 ml)
  9. filtrationThe solid was collected by filtration
  10. customtriturated with hot ethyl acetate (3 ml)
  11. filtrationThe solid was collected by filtration and air
  12. customdried

Sources & evidence

ORD record
ord-99fc1d2277064834b03cf74a98398a61
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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