Trifluoroacetic acid → 3-((2R)-2-(N-((2R)-2-methylamino-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionylamino)propyl acetate

HRID 1268596Notes

Reaction equation

HRID 1268596 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:50])[C@H:17]([N:25]([C:27](=[O:49])[C@H:28]([N:40](C(OC(C)(C)C)=O)[CH3:41])[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH3:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:10])[CH3:9]>ClCCl>[C:8]([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:50])[C@H:17]([N:25]([C:27](=[O:49])[C@H:28]([NH:40][CH3:41])[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH3:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 537513443-((2R)-2-(N-((2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-(2-naphthyl)-propionyl)-N-methylamino)-3-phenylpropionylamino)propyl acetate

Product 1

HCID 542776383-((2R)-2-(N-((2R)-2-methylamino-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionylamino)propyl acetateYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., trifluoroacetic acid (3 mL) was added to a solution of 3-((2R)-2-(N-((2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionylamino)propyl acetate (885 mg, 1.50 mmol) in dichloromethane (3 mL). The reaction mixture was stirred for 5 min. The solvents were removed in vacuo at 20° C. The residue was dissolved in dichloromethane (40 mL). The procedure was repeated twice. The crude product was purified by flash chromatography on silica (45 g) with dichloromethane/methanol/25% solution of ammonia in water (100:10:1) to give 497 mg of 3-((2R)-2-(N-((2R)-2-methylamino-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionylamino)propyl acetate.

Workup

  1. customThe solvents were removed in vacuo at 20° C
  2. dissolutionThe residue was dissolved in dichloromethane (40 mL)
  3. customThe crude product was purified by flash chromatography on silica (45 g) with dichloromethane/methanol/25% solution of ammonia in water (100:10:1)

Sources & evidence

ORD record
ord-0f6a2deaad894077bc696e11fba2de41
Source dataset
uspto-grants-2003_04
Patent number
US06555570B2

Reaction notes

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