Trifluoroacetic acid → HCID 71113011, compound

HRID 716825Notes

Reaction equation

HRID 716825 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:28]=[CH:27][C:23]3[CH2:24][O:25][CH2:26][C:22]=3[CH:21]=2)=[CH:15][CH:14]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:24]1[C:23]2[CH:27]=[CH:28][C:20]([O:19][C:16]3[CH:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[C@@H:9]([CH3:29])[NH2:5])=[CH:18][CH:17]=3)=[CH:21][C:22]=2[CH2:26][O:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734153HCID 131734153, compound2×

Product 1

HCID 71113011HCID 71113011, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl((1R)-2-{[4-(1,3-dihydro-2-benzofuran-5-yloxy)phenyl]amino}-1-methyl-2-oxoethyl)carbamate (Intermediate 76, 130 mg, 0.326 mmol) and TFA (1 ml) in dichloromethane (4 ml) was stirred under argon at room temperature. The reaction mixture was stirred at room temperature for 1 hour. The mixture was concentrated and the residue was purified by SCX to afford the title compound (94 mg), which was directly used in the next step.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by SCX

Sources & evidence

ORD record
ord-9faf11daa8554038a05770ccc6582126
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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