Hydrazine hydrate (1:1) → HCID 131731091, compound

HRID 1912377Notes

Reaction equation

HRID 1912377 reaction equation
[NH:1]([N:41]=[N+:42]=[N-:43])[C@H:2]([C:10]([NH:12][C@H:13]([C:29]([NH:31][C@H:32]([C:37]([O:39]C)=O)[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[NH2:45][NH2:46]>CO>[NH:1]([N:41]=[N+:42]=[N-:43])[C@H:2]([C:10]([NH:12][C@H:13]([C:29]([NH:31][C@H:32]([C:37]([NH:45][NH2:46])=[O:39])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])=[CH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131731092HCID 131731092, compound

Product 1

HCID 131731091HCID 131731091, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N3-Phe-Phe(4-NHBoc)-Leu-OMe (160 mg, 276 μmol) was dissolved in MeOH and hydrazine hydrate (800 μl, 16.6 mmol, 60 equiv.) was added and the mixture was stirred overnight. Co-evaporation with toluene (3×) yielded the title compound which was used without further purification. LC/MS: Rt 7.54 minutes (linear gradient 10->90% MeCN+0.1% TFA, 15 minutes), (ESI-MS (m/z): 581.13. 1H NMR (400 MHz, CD3OD): δ ppm 7.40-7.17 (m, 7H), 7.02 (d, J=8.5 Hz, 2H), 4.61 (t, J=7.0 Hz, 1H), 4.35 (t, J=7.3 Hz, 1H), 4.13 (dd, J=8.6, 4.8 Hz, 1H), 3.15 (dd, J=14.0, 4.7 Hz, 1H), 3.00-2.81 (m, 3H), 1.60-1.45 (m, 3H), 1.51 (s, 9H), 0.93 (d, J=6.0 Hz, 3H), 0.89 (d, J=5.9 Hz, 3H).

Workup

  1. customCo-evaporation with toluene (3×)

Sources & evidence

ORD record
ord-29d61cf7fc3b48e6822848fa1acb4939
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

Loading…