Trifluoroacetic acid → HCID 67772463, compound

HRID 1808806Notes

Reaction equation

HRID 1808806 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6](=[O:19])[C@@H:7]([NH:11]C(=O)OC(C)(C)C)[CH2:8][CH2:9][CH3:10])[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][C@@H:7]([CH2:8][CH2:9][CH3:10])[C:6]([N:4]1[CH2:3][CH:2]([OH:1])[CH2:5]1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67773202HCID 67773202, compound2×

Product 1

HCID 67772463HCID 67772463, compoundYield 176%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(3-hydroxyazetidin-1-yl)-1-oxopentan-2-ylcarbamate (Compound A2) (3.5 g, 12.8 mmol) in anhydrous DCM (50 mL) was added TFA (18 mL, 242 mmol) dropwise at 0° C. under N2(g). The reaction mixture was stirred at r.t for 2 h and then concentrated under reduced pressure. The residue was dissolved in DCM and concentrated under reduced pressure to remove the residue of TFA. This procedure was repeated twice with DCM and twice with MeOH. To the residue was added diethyl ether and decanted (×2). The crude product was dried in vacuo give the title compound (3.88 g) used in the next step without further purification. LCMS (M+H)+: 173.1

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM
  3. concentrationconcentrated under reduced pressure
  4. customto remove the residue of TFA
  5. additionTo the residue was added diethyl ether
  6. customdecanted (×2)
  7. dry with materialThe crude product was dried in vacuo

Sources & evidence

ORD record
ord-da8667eee4154dc5949227e68a8a0b4c
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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