Trifluoroacetic acid → HCID 73603253, compound

HRID 627036Notes

Reaction equation

HRID 627036 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([C@@H:12]1[N:20]([C:21](=[O:40])[C@@H:22]([NH:26][C:27](=[O:39])[C@@H:28]([N:30](C)[C:31](=O)OC(C)(C)C)[CH3:29])[CH:23]([CH3:25])[CH3:24])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([C@@H:12]1[N:20]([C:21](=[O:40])[C@@H:22]([NH:26][C:27](=[O:39])[C@@H:28]([NH:30][CH3:31])[CH3:29])[CH:23]([CH3:25])[CH3:24])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735259HCID 131735259, compound

Product 1

HCID 73603253HCID 73603253, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

For Example 9: To a solution of tert-butyl (R)-(2S)-1-((2S)-1-(2-(2-methoxyphenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (36 mg, 65.0 μmol, Eq: 1.00) in DCM (2 mL) was added TFA (1 mL, 13.0 mmol, Eq: 200) and the resulting solution was stirred at rt. After 2 h, the reaction mixture was concentrated in vacuo, the residue was treated with saturated aqueous NaHCO3 (5 mL) and the resulting mixture was extracted with DCM (2×5 mL). The combined organic layers were concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 4 g, 0% to 10% MeOH in DCM) to give (R)-1-[(S)-3-methyl-2-((S)-2-methylamino-propionylamino)-butyryl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-methoxyphenyl)-amide (22 mg), m/z=454 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with saturated aqueous NaHCO3 (5 mL)
  3. extractionthe resulting mixture was extracted with DCM (2×5 mL)
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 4 g, 0% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-f8d69a8dac774f479d6943d4c1d7b898
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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