Dichloromethane → HCID 67235119, compound

HRID 1023520Notes

Reaction equation

HRID 1023520 reaction equation
CC([N:5]([C@H:9]([CH3:29])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([O:27][CH3:28])[CH:21]=2)=[CH:15][CH:14]=1)=[O:11])C(=O)[O-])(C)C.ClCCl>>[CH3:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[C@@H:9]([CH3:29])[NH2:5])=[CH:14][CH:15]=2)=[CH:21][C:22]=1[O:27][CH3:28]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 86673581HCID 86673581, compound2×

Product 1

HCID 67235119HCID 67235119, compoundYield 97.1%

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-99f7d0be604a4fff836d8880b9c82df5
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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