Hydrochloric Acid → HCID 57500366, compound

HRID 2273538Notes

Reaction equation

HRID 2273538 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:12]=[C:13]([CH:40]=[CH:41][CH:42]=1)[C:14]([NH:16][C:17]1[C:18]([CH3:39])=[C:19]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([NH2:38])=[C:32]([CH:37]=2)[C:33]([O:35][CH3:36])=[O:34])=[O:27])[N:20]2[C:25]=1[CH:24]=[CH:23][CH:22]=[CH:21]2)=[O:15])(=O)C.Cl>O.CO.C(OCC)(=O)C.C(OCC)C>[NH2:38][C:31]1[CH:30]=[CH:29][C:28]([C:26]([C:19]2[N:20]3[C:25]([CH:24]=[CH:23][CH:22]=[CH:21]3)=[C:17]([NH:16][C:14](=[O:15])[C:13]3[CH:40]=[CH:41][CH:42]=[C:11]([OH:10])[CH:12]=3)[C:18]=2[CH3:39])=[O:27])=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57500364HCID 57500364, compound

Product 1

HCID 57500366HCID 57500366, compoundYield 84%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.46 g (3.30 mmol) of potassium carbonate dissolved in 4 ml of water is added to the suspension of 0.80 g (1.65 mmol) of methyl 5-[(1-{[3-(acetyloxy)benzoyl]-amino}-2-methylindolizin-3-yl)carbonyl]-2-aminobenzoate in 16 ml of methanol. The reaction medium is stirred at ambient temperature for 1 hour, it gradually becomes homogenized. It is diluted with ethyl acetate and acidified with a molar solution of hydrochloric acid. The two phases are separated. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The solid obtained is taken up in ethyl ether and then filtered and dried. 0.61 g (84%) of a greenish yellow powder is obtained.

Workup

  1. stirringit gradually becomes homogenized
  2. customThe two phases are separated
  3. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe solid obtained
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-3fba2870b98c4fd285442264ffc9b98d
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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