Sulfuric acid magnesium salt (1:1) → HCID 88932543, compound

HRID 1530622Notes

Reaction equation

HRID 1530622 reaction equation
[NH:1]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:2].[O-]S([O-])(=O)=O.[Mg+2].[Si:16]([O:23][CH2:24][CH:25]=O)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[Si:16]([O:23][CH2:24]/[CH:25]=[N:2]/[NH:1][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70091tert-Butyl carbazateHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehyde

Product 1

HCID 88932543HCID 88932543, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl hydrazinecarboxylate (2.5 g, 19 mmol), MgSO4 (11.4 g, 95.0 mmol), and 2-(tert-butyldimethylsilyloxy)acetaldehyde (9.9 g, 57 mmol) in DCM (100 mL) was heated to reflux overnight. The solid was filtered off and the filtrate was concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:5) to give (E)-tert-butyl 2-(2-(tert-butyldimethylsilyloxy)ethylidene)hydrazinecarboxylate (5.1 g, 94% yield) as colorless oil. LCMS (ESI) m/z: 233.3 [M-56+H+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with EtOAc/petroleum ether (1:5)

Sources & evidence

ORD record
ord-a90f56458e7e4123a2e0867757b578cd
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…