Reaction #1340591

ord-a6bd529fc550463e9448e15de3dc87a2

Reaction equation

NN.O
hydrazine monohydrate
[N-]=[N+]=NN[C@H](C=O)Cc1ccccc1
N3-Phe-H
COC(=O)[C@@H](N)CC(C)C
H-Leu-OMe
CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C
Boc-Leu-H
CN(C)C(On1nnc2ccc(Cl)cc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HCTU
→
CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NN=[N+]=[N-])C(=O)NN
Compound 38
CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NN=[N+]=[N-])C(=O)NN
N3-Phe-Leu-Leu-NHNH2

Reactants

NN.O
hydrazine monohydrate
—
tripeptide N3-Phe-Leu-Leu-OMe
—
peptide
[N-]=[N+]=NN[C@H](C=O)Cc1ccccc1
N3-Phe-H
COC(=O)[C@@H](N)CC(C)C
H-Leu-OMe
CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C
Boc-Leu-H
—
hydrazide
CN(C)C(On1nnc2ccc(Cl)cc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HCTU

Reagents

None

Solvents

CO
MeOH
Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThis compound was synthesized via general Boc-

Procedure

This compound was synthesized via general Boc-based peptide coupling procedures using HCTU from H-Leu-OMe, Boc-Leu-H and N3-Phe-H. The last step involved the introduction of the hydrazide by stirring of a mixture containing tripeptide N3-Phe-Leu-Leu-OMe (1.51 g, 3.49 mmol) and hydrazine monohydrate (30 eq., 105 mmol, 5.1 mL) in MeOH (30 mL) for 15 hours at room temperature. Compound 38 was obtained after coevaporation of the mixture with toluene (3×) as a colourless solid (yield: 1.51 g, 3.49 mmol, quant.). LC-MS: Rt (min): 6.87 (ESI-MS (m/z): 432.13 (M+H+)).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08455431B2uspto-grants-2013_06