Trifluoroacetic acid → HCID 86705899, compound

HRID 339259Notes

Reaction equation

HRID 339259 reaction equation
[NH2:1][C@@H:2]([C:66]([CH3:69])([CH3:68])[CH3:67])[C:3]([N:5]1[C@H:9]([C:10](=[O:22])[NH:11][C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)[CH2:8][C@H:7]([C:23]2[CH:32]=[C:31]3[C:26]([CH2:27][C@@H:28]([C:53](=[O:65])[NH:54][C@H:55]4[C:64]5[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=5)[CH2:58][CH2:57][CH2:56]4)[N:29]([C:33](=[O:52])[C@@H:34]([NH:44]C(OC(C)(C)C)=O)[C:35]([S:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])([CH3:37])[CH3:36])[CH2:30]3)=[CH:25][CH:24]=2)[CH2:6]1)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:44][C@H:34]([C:33]([N:29]1[C@H:28]([C:53](=[O:65])[NH:54][C@H:55]2[C:64]3[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=3)[CH2:58][CH2:57][CH2:56]2)[CH2:27][C:26]2[C:31](=[CH:32][C:23]([C@H:7]3[CH2:8][C@@H:9]([C:10](=[O:22])[NH:11][C@H:12]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH2:15][CH2:14][CH2:13]4)[N:5]([C:3](=[O:4])[C@@H:2]([NH2:1])[C:66]([CH3:69])([CH3:68])[CH3:67])[CH2:6]3)=[CH:24][CH:25]=2)[CH2:30]1)=[O:52])[C:35]([S:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705900HCID 86705900, compound

Product 1

HCID 86705899HCID 86705899, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(((R)-4-((S)-7-((3R,5S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-((tert-butoxycarbonyl)amino)-2-methyl-4-oxobutan-2-yl)thio)acetate (0.34 g, 0.35 mmol) in DCM (6 mL) was added TFA (1.2 mL, 15.6 mmol) slowly. The reaction mixture was stirred at rt for 40 min and concentrated in vacuo. The residue was basified with sat. aq. NaHCO3 solution to adjust the pH to 8-9. The resulting mixture was extracted with EtOAc (2×). The organic layers were combined and washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to afford the title compound as a white solid (0.30 g, 100%). MS (ESI+) m/z 865.5 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe resulting mixture was extracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b07273944e744b10a2ed69dc3d2c8d63
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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