HCID 53765562, compound → HCID 53918877, compound

HRID 849874Notes

Reaction equation

HRID 849874 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:20](=[O:47])[NH:21][C@@H:22]([C:34]1[N:38]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:37]=[N:36][N:35]=1)[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>C(Cl)Cl.FC(F)(F)C(O)=O>[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]([NH:21][C@@H:22]([C:34]1[N:38]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:37]=[N:36][N:35]=1)[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:47]

Participants

4

Reactant 1

HCID 53765562HCID 53765562, compound

Product 1

HCID 53918877HCID 53918877, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

((1R)-2-(2-Naphthyl)-1-((1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethylcarbamoyl)ethyl)carbamic acid tert-butyl ester (215 mg; 0.34 mmol) was dissolved in a mixture of methylene chloride (4 ml) and trifluoroacetic acid (2 ml) and stirred at room temperature for 30 min. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate and aqueous sodium hydrogencarbonate (10%; 10 ml). The phases were separated, the organic phase was dried (Magnesium sulfate) and the solvent removed in vacuo. The residue was chromatographed on silica (3×20 cm) using ethyl acetate as eluent to afford 152 mg of (2R)-2-amino-3-(2-naphthyl)-N-((1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethyl)propionamide.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried (Magnesium sulfate)
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed on silica (3×20 cm)

Sources & evidence

ORD record
ord-52ff6ca51e8a467e88c5d186eb862f03
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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