Trifluoroacetic acid → HCID 73603782, compound

HRID 627045Notes

Reaction equation

HRID 627045 reaction equation
[CH:1]1([C@H:7]([NH:28][C:29](=[O:42])[C@@H:30]([N:32]([CH2:40][CH3:41])C(=O)OC(C)(C)C)[CH3:31])[C:8](=[O:27])[N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11][C@H:10]2[C:18](=[O:26])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:20]1([NH:19][C:18]([C@H:10]2[N:9]([C:8](=[O:27])[C@H:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[NH:28][C:29](=[O:42])[C@@H:30]([NH:32][CH2:40][CH3:41])[CH3:31])[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11]2)=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735265HCID 131735265, compound

Product 1

HCID 73603782HCID 73603782, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-1-cyclohexyl-2-oxo-2-((S)-2-(phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethylamino)-1-oxopropan-2-yl(ethyl)carbamate (33 mg, 57.1 μmol, Eq: 1.00) was combined with DCM (3 mL) to give a colorless solution. TFA (1 mL, 13.0 mmol, Eq: 227) was added. After 30 min, the crude reaction mixture was concentrated in vacuo. The residue was taken up in DCM, washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give (S)-1-[(S)-2-Cyclohexyl-2-((S)-2-ethylamino-propionylamino)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid phenylamide as a white solid (23 mg), m/z=478 (M+H).

Workup

  1. customto give a colorless solution
  2. customthe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-049e30e74d5b44c0a00601df4a420c2e
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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