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

HRID 421938Notes

Reaction equation

HRID 421938 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([N:13]([CH3:43])[C@@H:14]1[CH2:21][N:20]2[C:22]3[CH:23]=[C:24]([C:35]([O:37][CH3:38])=[O:36])[CH:25]=[CH:26][C:27]=3[C:28]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:19]2[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=2[O:16][CH2:15]1)=[O:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][C:11]([N:13]([CH3:43])[C@@H:14]1[CH2:21][N:20]2[C:22]3[CH:23]=[C:24]([C:35]([O:37][CH3:38])=[O:36])[CH:25]=[CH:26][C:27]=3[C:28]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:19]2[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=2[O:16][CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66674302methyl(7R)-7-[[N-(tert-butoxycarbonyl)-beta-alanyl](methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674855methyl(7R)-7-[beta-alanyl(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-[[N-(tert-butoxycarbonyl)-β-alanyl](methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.15 M) in DCM was treated with TFA (10 eq.) and the resulting mixture was stirred for 4h at RT before removing all volatiles in vacuo. The residue was partitioned between EtOAc and sat aq NaHCO3 and the layers separated. The combined organics were washed with brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The product was used directly in the next step without further purification. (ES+) m/z 490 (M+H)+.

Workup

  1. custombefore removing all volatiles in vacuo
  2. customThe residue was partitioned between EtOAc
  3. customthe layers separated
  4. washThe combined organics were washed with brine
  5. dry with materialbefore being dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was used directly in the next step without further purification

Sources & evidence

ORD record
ord-becedec35f024a9c8a3553aade8ed04c
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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