Trifluoroacetic acid → (S)-Methyl 2-((S)-2-amino-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

HRID 339233Notes

Reaction equation

HRID 339233 reaction equation
C(OC([NH:8][C@@H:9]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:10]([N:12]1[C@H:21]([C:22](=[O:34])[NH:23][C@H:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26][CH2:25]2)[CH2:20][C:19]2[C:14](=[CH:15][C:16]([C:35]([O:37][CH3:38])=[O:36])=[CH:17][CH:18]=2)[CH2:13]1)=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@@H:9]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:10]([N:12]1[C@H:21]([C:22](=[O:34])[NH:23][C@H:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26][CH2:25]2)[CH2:20][C:19]2[C:14](=[CH:15][C:16]([C:35]([O:37][CH3:38])=[O:36])=[CH:17][CH:18]=2)[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705867(S)-Methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

Product 1

HCID 86705868(S)-Methyl 2-((S)-2-amino-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (1.21 g, 2.09 mmol) in CH2Cl2 (13.9 mL) was charged with TFA (3.49 mL) at room temperature. After 40 min, the reaction mixture was quenched carefully with sat. NaHCO3 and then extracted with EtOAc (3×). The combined extracts were washed with sat. NaCl, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (0.97 g, 2.02 mmol, 97%) as a light yellow foam, which was used without further purification. MS (ESI+) m/z 478.2 (M+H)+.

Workup

  1. customthe reaction mixture was quenched carefully with sat. NaHCO3
  2. extractionextracted with EtOAc (3×)
  3. washThe combined extracts were washed with sat. NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6c072d450174c3795fd9d587ed8bf60
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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