tert-Butyl carbazate → HCID 131734721, compound

HRID 1774525Notes

Reaction equation

HRID 1774525 reaction equation
[CH:1]1([C:4](=O)[CH:5]([CH3:13])[C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[NH:16][NH2:17]>C(O)C>[CH:1]1([C:4]2[N:16]([C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:17]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]=2[CH3:13])[CH2:3][CH2:2]1.[CH:1]1([C:4]2[C:5]([CH3:13])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:16]([C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:17]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 64919879HCID 64919879, compound

Product 1

HCID 131734721HCID 131734721, compoundYield 190.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

49.2 g of ethyl 4-cyclopropyl-3-methyl-2,4-dioxobutanoate 1-13-1 (248 mmol, 1.0 eq.) and 32.81 g of tert-butyl carbazate were refluxed for 4 hours in 200 mL of ethanol. The mixture was concentrated in vacuo. The residue was purified by flash chromatography to provided 2.17 g (7.37 mmol, 3.0%) of analytically pure target compound and 69.6 g (236 mmol, 95%) of a mixture of regioisomers which was used for the following step without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-13afa3bfab9f4792acab6dd3b2713710
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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