Water → (3-{3-[4-Amino-3-(methoxycarbonyl)-benzoyl]-2-methylindolizin-1-yl}phenoxy)acetic acid

HRID 2273551Notes

Reaction equation

HRID 2273551 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]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[CH:24]=3)[C:15]=2[CH3:38])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O>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]([C:23]3[CH:24]=[C:25]([CH:26]=[CH:27][CH:28]=3)[O:29][CH2:30][C:31]([OH:33])=[O:32])[C:15]=2[CH3:38])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 962WaterHCID 57500396Methyl 2-amino-5-({1-[3-(2-tert-butoxy-2-oxoethoxy)phenyl]-2-methylindolizin-3-yl}carbonyl)benzoate

Product 1

HCID 57500399(3-{3-[4-Amino-3-(methoxycarbonyl)-benzoyl]-2-methylindolizin-1-yl}phenoxy)acetic acidYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of 3.68 g (6.65 mmol) of methyl 2-amino-5-({1-[3-(2-tert-butoxy-2-oxoethoxy)phenyl]-2-methylindolizin-3-yl}carbonyl)benzoate in 11 ml of trifluoroacetic acid and 35 ml of dichloromethane at ambient temperature for 4 hours. The reaction medium is poured into water and the mixture is extracted with dichloromethane. The organic phase is partially concentrated, and the yellow precipitate formed is filtered and washed with diisopropyl ether and then dried, to give 2.75 g (92%) of a yellow powder.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. concentrationThe organic phase is partially concentrated
  3. customthe yellow precipitate formed
  4. filtrationis filtered
  5. washwashed with diisopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-77d8464de035465786e4bd70923a64f7
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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