Trifluoroacetic acid → (αS)-α-[[(9H-Fluoren-9-ylmethoxy)carbonyl]methylamino]-1-naphthalenepropanoic acid

HRID 625863Notes

Reaction equation

HRID 625863 reaction equation
[C:1]1([CH2:11][C@H:12]2[C:16](=[O:17])[O:15][CH2:14][N:13]2[C:18]([O:20][CH2:21][CH:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH:24]1[C:23]2[CH:22]([CH2:21][O:20][C:18]([N:13]([CH3:14])[C@@H:12]([CH2:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[C:16]([OH:17])=[O:15])=[O:19])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 117599850HCID 117599850, compound

Product 1

HCID 66601204(αS)-α-[[(9H-Fluoren-9-ylmethoxy)carbonyl]methylamino]-1-naphthalenepropanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(9H-fluoren-9-yl)methyl 4-(naphthalen-1-ylmethyl)-5-oxooxazolidine-3-carboxylate (0.750 g, 1.669 mmol) in DCM (8.0 ml) was added trifluoroacetic acid (8.0 mL, 104 mmol) followed by triethylsilane (0.799 ml, 5.01 mmol). The reaction mixture was allowed to stir at room temperature for 24 hours. Reaction mixture was dried on rotovap. The crude oil was dissolved in 15.0 mL of DCM and evaporated on rotovap twice. The crude product was obtained as an off-white gum and was purified by silica gel chromatography using dichloromethane and methanol as eluant. The desired product, (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(naphthalen-1-yl)propanoic acid, was obtained as a colorless gum (0.692 g, 46%).

Workup

  1. customReaction mixture
  2. customwas dried on rotovap
  3. dissolutionThe crude oil was dissolved in 15.0 mL of DCM
  4. customevaporated on rotovap twice
  5. customThe crude product was obtained as an off-white gum
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-fff066f4ec5944d18de43204c8aa41e9
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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