Trifluoroacetic acid → HCID 68769905, compound

HRID 2265263Notes

Reaction equation

HRID 2265263 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:20]C(OC(C)(C)C)=O)[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH2:20])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68770244HCID 68770244, compound

Product 1

HCID 68769905HCID 68769905, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-3,3-bis-(4-chloro-phenyl)-propionic acid methyl ester (0.23 g, 0.54 mmol) in DCM (3 mL) at rt was added TFA (1 mL). After 2 h, the mixture was concentrated, diluted with water, and extracted with DCM (3×). The combined organic extracts were dried (Na2SO4) and concentrated to provide 100 mg (57%) of the amine as a tan viscous oil. MS (ESI+): mass calcd. for C16H15Cl2NO2, 323.05; m/z found, 324 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.32-7.19 (m, 8H), 4.26 (d, J=8.0, 1H), 4.15 (app q, J=7.4, 1H), 3.57 (s, 3H), 1.46 (br d, J=6.6, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with DCM (3×)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3a5c6c9bded48679f27a75164088e24
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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