Dichloromethane → HCID 67235119, compound

HRID 1505318Notes

Reaction equation

HRID 1505318 reaction equation
[CH3:1][C@@H:2]([NH:22]C(=O)OC(C)(C)C)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([O:20][CH3:21])[CH:14]=2)=[CH:8][CH:7]=1)=[O:4].ClCCl>>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C@@H:2]([CH3:1])[NH2:22])=[CH:7][CH:8]=2)=[CH:14][C:15]=1[O:20][CH3:21]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 68322429HCID 68322429, compound2×

Product 1

HCID 67235119HCID 67235119, compoundYield 97.3%

Procedure

To a solution of 1,1-dimethylethyl {(1R)-1-methyl-2-[(4-{[4-methyl-3-(methyloxy)phenyl]oxy}phenyl)amino]-2-oxoethyl}carbamate (Intermediate 21, 300 mg) in dry dichloromethane (7.5 mL) TFA (2.5 mL, 32.4 mmol) was slowly added and the reaction mixture was stirred for 1.5 hours at room temperature. The solvent and the excess of TFA were evaporated and the residue was purified by SCX cartridge (10 g) to afford the title compound as an orange oil (219 mg).

Workup

  1. customThe solvent and the excess of TFA were evaporated
  2. customthe residue was purified by SCX cartridge (10 g)

Sources & evidence

ORD record
ord-5fc28f03edb34c5c944f156534275047
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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