Trifluoroacetic acid → (2R)-2-amino-N-{6-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide

HRID 527666Notes

Reaction equation

HRID 527666 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:6][C:5]2[C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:24][C@H:21]([CH2:22][CH3:23])[C:19]([NH:18][C:15]1[CH:16]=[N:17][C:12]([O:11][C:7]2[C:5]3[CH2:6][C:2]([CH3:1])([CH3:32])[O:3][C:4]=3[CH:10]=[CH:9][CH:8]=2)=[CH:13][CH:14]=1)=[O:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86698460tert-butyl N-[(1R)-1-[[6-[(2,2-dimethyl-3H-benzofuran-4-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate2×

Product 1

HCID 67958761(2R)-2-amino-N-{6-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl N-[(1R)-1-[[6-[(2,2-dimethyl-3H-benzofuran-4-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate (Intermediate 208, 14 mg, 0.032 mmol) in dry dichloromethane (1 ml) at 0° C., TFA (98 μl, 1.268 mmol) was slowly added and the reaction mixture was stirred for 4 hours at the same temperature. Some more dichloromethane (4 ml) was added to the reaction mixture. An aqueous saturated aqueous solution of NaHCO3 was then added while the pH was allowed to reach ˜8. Two phases were separated and the aqueous one was further extracted with DCM (3×3 ml). Combined organic layers were dried over Na2SO4, filtrated and evaporated affording the title compound (10 mg).

Workup

  1. customTwo phases were separated
  2. extractionthe aqueous one was further extracted with DCM (3×3 ml)
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-179f9c0fc39b40dbbc86416d69c536ed
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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