Sodium Bicarbonate → HCID 57500361, compound

HRID 2273536Notes

Reaction equation

HRID 2273536 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]3)=[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])[CH:26]=3)[C:15]=2[CH3:40])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.ClCCl>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]3)=[C:16]([O:23][CH2:24][C:25]3[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=3)[O:31][CH2:32][C:33]([OH:35])=[O:34])[C:15]=2[CH3:40])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 57500360HCID 57500360, compound

Product 1

HCID 57500361HCID 57500361, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of 0.87 g (1.60 mmol) of methyl 2-amino-5-[(1-{[3-(2-tert-butoxy-2-oxoethoxy)benzyl]oxy}-2-methylindolizin-3-yl)carbonyl]benzoate in 3.0 ml of trifluoroacetic acid and 16 ml of dichloromethane at ambient temperature is stirred for 4 hours at ambient temperature. The reaction medium is poured into a saturated aqueous solution of sodium bicarbonate and the mixture is washed with ethyl acetate. The aqueous phase is acidified with a saturated aqueous solution of potassium hydrogen sulphate and then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. 0.69 g (88%) of a green solid is obtained.

Workup

  1. washthe mixture is washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  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

Sources & evidence

ORD record
ord-aac46df2d2044f04bbccbf7924ee358f
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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