L-Leucine → HCID 69152081, compound

HRID 1744090Notes

Reaction equation

HRID 1744090 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1.[NH2:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[C:7]1([N:6]2[C:2]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[N:3][N:4]=[N:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6106L-LeucineHCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-

Product 1

HCID 69152081HCID 69152081, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 5-chloro-1-phenyl-1H-tetrazole (2.80 g, 15.5 mmol), L-leucine (3.36 g, 25.6 mmol) and potassium carbonate (6.43 g, 46.5 mmol) in isopropanol (20 mL) was heated to reflux for 3 h. The mixture was cooled and partitioned between ethyl acetate and 1 M HCl. The organic phase was washed with brine and concentrated. Purification by flash chromatography on silicic acid (50% ethyl acetate/hexanes) provided 1.57 g of N-(1-phenyl-1H-tetraazol-5-yl)-L-leucine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. temperatureThe mixture was cooled
  4. custompartitioned between ethyl acetate and 1 M HCl
  5. washThe organic phase was washed with brine
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silicic acid (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a72e880a31db47958f876ce7c9a30ea3
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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