Trifluoroacetic acid → HCID 68283949, compound

HRID 1527194Notes

Reaction equation

HRID 1527194 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[N:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C:17]([C:10]1[N:11]2[C:16]([CH:15]=[CH:14][CH:13]=[CH:12]2)=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=1)=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68284522HCID 68284522, compound

Product 1

HCID 68283949HCID 68283949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of indolizine-1,3-dicarboxylic acid 3-benzyl ester 1-tert-butyl ester (400 mg, 1.14 mmol) and TFA (872 μl, 11.4 mmol) in CH2Cl2 (10 mL) was stirred at RT overnight. The reaction mixture was concentrated and the crude solid was taken-up in a mixture of MeOH and CH2Cl2, the precipitate was filtered-off and washed with a minimum of MeOH to give the desired compound as a white powder. The filtrate was concentrated and purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 95:5) to give again the desired compound. TLC, Rf (CH2Cl2/MeOH 9:1)=0.6; MS (LC/MS): 296.0 [M+H]+ 294.1 [M−H]−; tR (HPLC conditions a): 3.64 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe crude solid was taken-up in a mixture of MeOH and CH2Cl2
  3. washwashed with a minimum of MeOH

Sources & evidence

ORD record
ord-eb48bf246a1040448c05369b14089545
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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