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

HRID 612370Notes

Reaction equation

HRID 612370 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.[NH2:21][C@H:22](C(O)=O)CCCNC(=N)N.C[N-]OC.[CH3:37][CH2:38]N(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=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:21][N:9]=2)[CH:3]=[CH:4][CH:6]=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10968127HCID 10968127, compoundHCID 53630747Methoxy-methyl amideHCID 178418600HCID 178418600, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-59a465c951ce4a20b75bad233928a522
Source dataset
uspto-grants-1999_12
Patent number
US06004933

Reaction notes

Loading…