Trifluoroacetic acid → HCID 18394421, compound

HRID 366261Notes

Reaction equation

HRID 366261 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:21](=[O:40])[N:22]([C@@H:24]([CH2:32][NH:33][C:34]([NH:36][CH:37]1[CH2:39][CH2:38]1)=[S:35])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:23])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:25]([C@@H:24]([N:22]([CH3:23])[C:21](=[O:40])[C@H:9]([NH:7][CH3:6])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[CH2:32][NH:33][C:34]([NH:36][CH:37]1[CH2:38][CH2:39]1)=[S:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54124732HCID 54124732, compound

Product 1

HCID 18394421HCID 18394421, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-((1R)-1-(N-((1R)-1-((3-Cyclopropylthioureido)methyl)-2-phenylethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamic acid tert-butylester (579 mg, 1.01 mmol) was dissolved in dichloromethane (2 ml). The solution was cooled to 0° C. Trifluoroacetic acid (2 ml) was added. The solution was stirred for 5 min. The solvents were removed in vacuo without warming. The residue was dissolved in dichloromethane (100 ml) and the solvent was removed in vacuo. This latter procedure was repeated two times. The crude product was purified by flash chromatography on silica (45 g) using dichloromethane/methanol/25% aqueous ammonia 100:10:1 as eluent to give 201 mg of (2R)-N-((1R)-1-benzyl-2-(3-cyclopropylthioureido)ethyl)-N-methyl-2-methylamino-3-(2-naphthyl)propionamide.

Workup

  1. customThe solvents were removed in vacuo
  2. temperaturewithout warming
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (45 g)

Sources & evidence

ORD record
ord-f654a9541d2b456a82107f828b9973a4
Source dataset
uspto-grants-2000_10
Patent number
US06127391

Reaction notes

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