Methyl (S)-(-)-2-Isocyanato-3-methylbutyrate → methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate

HRID 1924378Notes

Reaction equation

HRID 1924378 reaction equation
[C:1]([NH:7][NH2:8])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[O:9]=[C:10]=[N:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14]>O1CCOCC1>[C:1]([NH:7][NH:8][C:10]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:9])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 10397066Methyl (S)-(-)-2-Isocyanato-3-methylbutyrateHCID 12826231Pent-4-enehydrazide

Product 1

HCID 44549344methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1.6 M solution of pent-4-enohydrazide (from Step 2) in dioxane, 1 eq. of methyl N-(oxomethylene)-L-valinate, (prepared as described in J. Het. Chem. 1990, 739) was added. After sting at RT for 3 h, volatiles were removed in vacuo, to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 9.55 (d, J 2.1, 1H), 7.86 (d, J 2.2, 1H), 6.48 (d, J 8.1, 1H), 5.86-5.76 (m, 1H), 5.04 (dd, J 17.2, 1.5, 1H), 4.96 (d, J 18.2, 10.3, 1H), 4.09 (dd, J 8.7, 5.7, 1H), 3.64 (s, 3H), 2.32-2.24 (m, 2H), 2.22-2.15 (m, 2H), 2.08-1.90 (m, 1H), 0.94 (d, J 3.9, 3H), 0.92 (d, J 3.9, 3H). MS (ES+) C12H21N3O4 requires: 271 found: 272 (M+H+).

Workup

  1. additionwas added
  2. customvolatiles were removed in vacuo

Sources & evidence

ORD record
ord-3649b9d352aa436497a42b2e5bbd8371
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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