Magnesium Carbonate → Tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate

HRID 588499

Reaction equation

HRID 588499 reaction equation
[NH2:1][C:2](=[S:13])[C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].Cl[CH:15]([CH:18]=O)[CH:16]=[O:17].C(=O)([O-])[O-].[Mg+2]>O1CCOCC1>[CH:16]([C:15]1[S:13][C:2]([CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH3:4])=[N:1][CH:18]=1)=[O:17]

Participants

5

Reactant 3

HCID 11029Magnesium CarbonateHCID 147646ChloromalonaldehydeHCID 10932591tert-butyl N-[(1S)-1-carbamothioylethyl]carbamate

Product 1

HCID 86657335Tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamateYield 71.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (S)-tert-butyl 1-amino-1-thioxopropan-2-ylcarbamate (6.9 g, 0.03 mol), 2-chloromalonaldehyde (5.2 g, 0.049 mol) and magnesium carbonate (2.76 g, 0.03 mol) in 1,4-dioxane (400 mL) was heated at 60° C. for 3 hours and further at room temperature overnight. The reaction mixture was concentrated and the residue purified by column chromatography (50-80% EtOAc/hexane) to afford tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate (5.5 g, 64%). LC-MS: (FA) ES+ 257.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by column chromatography (50-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-f7575ef37cc1429288f17fcac56035ab
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Linked notes

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