Trifluoroacetic acid → HCID 89814971, compound

HRID 1487104Notes

Reaction equation

HRID 1487104 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([NH:13]C(=O)OC(C)(C)C)[CH:10]=[CH:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:13][C:9]1[CH:8]=[C:7]([C:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 40013524HCID 40013524, compound

Product 1

HCID 89814971HCID 89814971, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (3-(azetidine-1-carbonyl)phenyl)carbamate (600 mg, 2.171 mmol) in DCM (5.0 ml) was added trifluoroacetic acid (0.167 ml, 2.171 mmol) at 0° C. under nitrogen atmosphere. Reaction was stirred at room temperature for 1 hr. Solvent evaporated up to dryness and the residual solid was dissolved in DCM (20 ml) and washed with saturated solution of NaHCO3. DCM layer was dried over sodium sulphate and evaporated under vacuum. Resulting solid was washed with pentane and ether to give the titled compound (310 mg).

Workup

  1. customReaction
  2. customSolvent evaporated up to dryness
  3. dissolutionthe residual solid was dissolved in DCM (20 ml)
  4. washwashed with saturated solution of NaHCO3
  5. dry with materialDCM layer was dried over sodium sulphate
  6. customevaporated under vacuum
  7. customResulting solid
  8. washwas washed with pentane and ether

Sources & evidence

ORD record
ord-7017c8ed4f564b7a86a23455adfd0552
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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