Hydrazine hydrate (1:1) → HCID 131730606, compound

HRID 1253409Notes

Reaction equation

HRID 1253409 reaction equation
CN(C(O[N:9]1[N:18]=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:26][C@H:27]([C:32]([O:34]C)=O)[CH2:28][CH:29]([CH3:31])[CH3:30].[NH:36]([C:44]([O:46]C(C)(C)C)=O)[C@H:37]([CH:42]=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40].[NH:51]([N:62]=[N+:63]=[N-:64])[C@H:52](C=O)[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.O.NN>CO.C1(C)C=CC=CC=1>[NH:51]([N:62]=[N+:63]=[N-:64])[C@H:52]([C:44]([NH:36][C@H:37]([C:42]([NH:26][C@H:27]([C:32]([NH:9][NH2:18])=[O:34])[CH2:28][CH:29]([CH3:30])[CH3:31])=[O:43])[CH2:38][CH:39]([CH3:40])[CH3:41])=[O:46])[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

8

Reactant 5

HCID 24654Hydrazine hydrate (1:1)HCID 65105(+)-L-Leucine methyl esterHCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 131730607HCID 131730607, compound

Product 1

HCID 131730606HCID 131730606, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

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+)).

Workup

  1. customThis compound was synthesized via general Boc-

Sources & evidence

ORD record
ord-a6bd529fc550463e9448e15de3dc87a2
Source dataset
uspto-grants-2013_06
Patent number
US08455431B2

Reaction notes

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