Dichloromethane → (2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide

HRID 1505350Notes

Reaction equation

HRID 1505350 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:16]([C@H:18]([NH:21]C(=O)OC(C)(C)C)[CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:29][CH3:30].ClCCl>>[NH2:21][C@H:18]([CH2:19][CH3:20])[C:16]([NH:15][C:12]1[CH:13]=[N:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:29][CH3:30])[CH:4]=2)=[CH:10][CH:11]=1)=[O:17]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 679668461,1-dimethylethyl ((1R)-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate2×

Product 1

HCID 67236842(2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamideYield 91.8%

Procedure

To a solution of 1,1-dimethylethyl ((1R)-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 64, 175 mg) in dry dichloromethane (DCM) (6 mL) TFA (2 mL, 26.0 mmol) was slowly added and the reaction mixture was stirred for 1 h at room temperature. The solvent and the excess of TFA were evaporated and the residue was purified by SCX cartridge (5 g) to afford the title compound as a colourless solid (122 mg).

Workup

  1. customThe solvent and the excess of TFA were evaporated
  2. customthe residue was purified by SCX cartridge (5 g)

Sources & evidence

ORD record
ord-dde165cc02674df594b9b4eb3c82faf5
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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