Tetrahydrofuran → HCID 18659598, compound

HRID 1608512Notes

Reaction equation

HRID 1608512 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:25]([OH:27])=O)[CH2:21][CH2:22][CH2:23][CH3:24])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=[O:34])C=1.C([N-]C(C)C)(C)C.[Li+].[Cl-].[NH4+].[CH2:50]1[CH2:54][O:53][CH2:52][CH2:51]1>CCCCCC.C(OCC)(=O)C>[CH2:52]([O:53][C:54]([CH2:50][C:25]([CH:20]([NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:27])=[O:34])[CH3:51]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 2724682Lithium diisopropylamideHCID 15284423HCID 15284423, compound

Product 1

HCID 18659598HCID 18659598, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

In 10 ml of anhydrous THF was dissolved 1.3 g of N-benzyloxycarbonyl-L-leucyl-L-norleucine prepared in the same manner as in Example 1-(b), and 680 mg of carbodiimidazole was added thereto, followed by refluxing for 2 hours. The reaction mixture was cooled to -78° C., and 6.1 ml of a 2M lithium diisopropylamide solution in hexane and 1.05 ml of anhydrous ethyl acetate were added thereto, followed by stirring for 30 minutes. After completion of the reaction, the reaction mixture was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organlc layer was washed with a saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by medium-pressure column chromatography on silica gel to obtain 540 mg of the titled compound as a yellow solid.

Workup

  1. temperatureby refluxing for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organlc layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-7cbe4bfd76874ffd83222be47b1dc96f
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

Loading…