Trifluoroacetic acid → HCID 123840104, compound

HRID 511029Notes

Reaction equation

HRID 511029 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:14]1[C:15]([O:33][CH3:34])=[C:16]([CH:22]2[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]2)[C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO.CCOC(C)=O>[NH:24]1[CH2:25][CH:22]([C:16]2[C:15]([O:33][CH3:34])=[C:14]([CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH3:13])[CH:19]=[C:18]([Cl:20])[C:17]=2[Cl:21])[CH2:23]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86666947HCID 86666947, compound

Product 1

HCID 123840104HCID 123840104, compoundYield 112.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 3-[3-(1-{[(benzyloxy)carbonyl]amino}ethyl)-5,6-dichloro-2-methoxyphenyl]azetidine-1-carboxylate (200 mg, 0.39 mmol, from Example 194, Step 6) in methylene chloride (10 mL) was treated with trifluoroacetic acid (5 mL) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated to give a residue that was dissolved in methanol (˜20 mL) and treated with saturated sodium bicarbonate solution (pH˜8). The methanol was then removed in vacuo to give an aqueous suspension that was diluted with EtOAc. The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the desired product (180 mg, 98%) that was used without further purification. LCMS for C20H23Cl2N2O3 (M+H)+: m/z=409.1, 411.1. Found: 409.1, 411.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a residue that
  3. customThe methanol was then removed in vacuo
  4. customto give an aqueous suspension that
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fa6af3187cb3438d8cdbb6beaaac0052
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

Loading…