Diisopropylethylamine → 1,3,4-Oxadiazole, 2-phenyl-

HRID 1274810Notes

Reaction equation

HRID 1274810 reaction equation
N(C(C)=O)[C@H:2]([C:7]([NH:9][C@H](C(O)=O)CC(C)C)=[O:8])[CH2:3][CH:4]([CH3:6])C.C[CH2:22][N:23](C(C)C)C(C)C.CN(C(ON1N=N[C:40]2C=CC=C[C:39]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:2]1([C:7]2[O:8][CH:22]=[N:23][N:9]=2)[CH:3]=[CH:4][CH:6]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10968127Acetyl-L-leucyl-L-leucine

Product 1

HCID 132171,3,4-Oxadiazole, 2-phenyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetyl-L-leucyl-L-leucyl-arginine(Mtr) (N-methyl)-(N-Methoxy)-amide: Acetyl-Leu-Leu-OH (133 mg) and arginine (Mtr)-N-methyl-N-methoxy amide (200 mg) were dissolved in 10 mL of DMF and were treated with 243 uL of DIEA and 212 mg of HBTU. The reaction stirred at room temperature for 15 hours and was worked up according to method A. Drying over Na2SO4, rotary evaporation of the solvent and flash chromatography on silica gel (50% acetone in hexane) provided 270 mg of the title compound as a foam.

Workup

  1. dry with materialDrying over Na2SO4, rotary evaporation of the solvent and flash chromatography on silica gel (50% acetone in hexane)

Sources & evidence

ORD record
ord-259da654620547c3b790ceffc82cf6fb
Source dataset
uspto-grants-2000_12
Patent number
US06159938

Reaction notes

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