Trifluoroacetic acid → HCID 53765850, compound

HRID 849878Notes

Reaction equation

HRID 849878 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:20](=[S:22])[NH2:21])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@H:8]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[C:20](=[S:22])[NH2:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54313871HCID 54313871, compound

Product 1

HCID 53765850HCID 53765850, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((1R)-2-(2-Naphthyl)-1-thiocarbamoylethyl)carbamic acid tert-butylester (0.45 g; 1.36 mmol) was dissolved in methylene chloride (1.5 ml) and trifluoroacetic acid (1.5 ml) was added. The reaction mixture was stirred for 40 min at room temperature. The solvent was removed in vacuo and the residue was dissolved in methylene chloride. Aqueous sodium hydrogencarbonate was added until basic reaction and the aqueous phase was extracted with methylene chloride (3×15 ml). The combined organic phases were dried (MgSO4) and the solvent was removed in vacuo to afford 0.311 g of (2R)-2-amino-3-(2-naphthyl)propionthioamide.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. additionAqueous sodium hydrogencarbonate was added until basic reaction
  4. extractionthe aqueous phase was extracted with methylene chloride (3×15 ml)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-727711c0e1244854852df6479a3eeb82
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

Loading…