Trifluoroacetic acid → methyl(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421944Notes

Reaction equation

HRID 421944 reaction equation
C(OC([NH:8][CH2:9][CH2:10][N:11]([CH3:41])[C@@H:12]1[CH2:19][N:18]2[C:20]3[CH:21]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:23]=[CH:24][C:25]=3[C:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:17]2[C:16]2[CH:37]=[CH:38][CH:39]=[CH:40][C:15]=2[O:14][CH2:13]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][N:11]([CH3:41])[C@@H:12]1[CH2:19][N:18]2[C:20]3[CH:21]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:23]=[CH:24][C:25]=3[C:26]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)=[C:17]2[C:16]2[CH:37]=[CH:38][CH:39]=[CH:40][C:15]=2[O:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53381224methyl(7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674669methyl(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl(7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 1, Step 6) (0.1 M) in DCM was treated with an excess of TFA (>50 eq.). The mixture was stirred at RT for 1 h. All the volatiles were then removed in vacuo and the residue treated with a solution of HCl/Et2O (2 M) and the resulting mixture concentrated in vacuo. The product was used in the next step without further purification. (ES+) m/z 462 (M+H)+.

Workup

  1. customAll the volatiles were then removed in vacuo
  2. additionthe residue treated with a solution of HCl/Et2O (2 M)
  3. concentrationthe resulting mixture concentrated in vacuo
  4. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-1e7d456365e74a68b7e934c60da55dd3
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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