Trifluoroacetic acid → HCID 21489497, compound

HRID 876355Notes

Reaction equation

HRID 876355 reaction equation
C(OC(N1CC(OC(=O)C)CC1C[C:21]1[C:29]2[C:24](=[CH:25][C:26](F)=[CH:27][CH:28]=2)[NH:23][CH:22]=1)=O)C1C=CC=CC=1.[C:31](O)([C:33](F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[NH:23]1[C:31]2[C:33](=[CH:29][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:22]1[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 66852222HCID 66852222, compound

Product 1

HCID 21489497HCID 21489497, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
3 °C

Procedure

A solution containing 8 (2.9 g, 7.1 mmol) in EtOAc (ca. 5 mL) was cooled in an ice-bath and pre-cooled TFA (20.3 mL) was added in one portion. The resulting yellow-colored solution was stirred at 2-4° C. After 4.75 h, the cold reaction mixture was transferred (via canula) with stirring into a pre-cooled mixture of EtOAc (30 mL), and 25% aq. K2CO3 (80.7 g). The aqueous layer was separated and extracted with EtOAc (3×30 mL) and the combined organic extracts were washed with 10% aq. Na2CO3 (30 g). The organic solution was concentrated in vacuo and azeotropically dried using anhydrous EtOAc to afford 2.95 g of indolylindoline diastereomers as a yellow-colored foam which was used directly in the next reaction. Mass spectrum (ESI), m/z 821.3 [(M)+; calcd for C46H46F2N4O8: 820.9].

Workup

  1. temperaturewas cooled in an ice-bath
  2. additionwas added in one portion
  3. customthe cold reaction mixture
  4. customThe aqueous layer was separated
  5. extractionextracted with EtOAc (3×30 mL)
  6. washthe combined organic extracts were washed with 10% aq. Na2CO3 (30 g)
  7. concentrationThe organic solution was concentrated in vacuo
  8. customazeotropically dried

Sources & evidence

ORD record
ord-83b4bfa2071a40d98506e3d4bd4e5472
Source dataset
uspto-grants-2015_03
Patent number
US08986993B2

Reaction notes

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