Trifluoroacetic acid → HCID 54555847, compound

HRID 849880Notes

Reaction equation

HRID 849880 reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:20](=[O:37])[NH:21][C@@H:22]([C:34](=[S:36])[NH2:35])[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)[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>[CH3:6][NH: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]([NH:21][C@@H:22]([C:34](=[S:36])[NH2:35])[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54077897HCID 54077897, compound

Product 1

HCID 54555847HCID 54555847, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methyl-N-((1R)-2-(2-naphthyl)-1-((1R)-2-(2-naphthyl)-1-thiocarbamoylethylcarbamoyl)ethyl)carbamic acid tert-butylester (0.25 g; 0.462 mmol) was dissolved in methylene chloride (1.5 ml) and trifluoroacetic acid (1.5 ml) was added. The reaction mixture was stirred 1 h at RT. The solvent was removed in vacuo and the residue was dissolved in methylene chloride (5 ml) and washed with aqueous sodium hydrogencarbonate (5 ml). The organic phase was dried (Magnesium sulfate) and the solvent was removed in vacuo to afford 0.201 g of (2R)-2-methylamino-3-(2-naphthyl)-N-((1R)-2-(2-naphthyl)-1-thiocarbamoylethyl)propionamide.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride (5 ml)
  3. washwashed with aqueous sodium hydrogencarbonate (5 ml)
  4. dry with materialThe organic phase was dried (Magnesium sulfate)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-78ab087e415c4ea59108b9793641885b
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

Loading…