Trifluoroacetic acid → HCID 89668315, compound

HRID 1482248Notes

Reaction equation

HRID 1482248 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([C:29](=[O:36])[N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[CH:13][CH:12]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[CH:50]1[C:62]2[CH:61]([CH2:63]OC(ON3C(=O)CCC3=O)=O)[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:54]=2[CH:53]=[CH:52][CH:51]=1>C(Cl)Cl>[CH:50]1[C:62]2[CH:61]([CH2:63][O:5][C:6]([NH:8][C@H:9]([C:29](=[O:36])[N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[CH2:10][C:11]3[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:16]=3)=[O:7])[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:54]=2[CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 89668519HCID 89668519, compound

Product 1

HCID 89668315HCID 89668315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (S)-6-(4-(2-((tert-butoxycarbonyl)amino)-3-oxo-3-(piperidin-1-yl)propyl)phenyl)hexanoate (Compound SP426) (5.65 g, 11.24 mmol) was dissolved in DCM (30.0 ml), trifluoroacetic acid (15.0 ml, 195 mmol) was added and the mixture was stirred for 30 minutes at room temperature, after which the reaction solution was concentrated under reduced pressure. The resulting residue was dissolved in dioxane (40 ml) and a 10% aqueous sodium carbonate solution (80 ml), N-(9-fluorenylmethoxycarbonyloxy)-succinimide (3.68 g, 10.90 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed with diethyl ether, made acidic by adding a 5 N aqueous HCl solution and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound SP427 (6.39 g, 100%).

Workup

  1. concentrationafter which the reaction solution was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in dioxane (40 ml)
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. washThe reaction solution was washed with diethyl ether
  5. additionby adding a 5 N aqueous HCl solution
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8012aa0412e44209a48b6fbec1eb7c7f
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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