Calcium Carbonate → Ethyl 2-{[(tert-butoxycarbonyl)amino]methyl}-1,3-thiazole-4-carboxylate

HRID 1376589Notes

Reaction equation

HRID 1376589 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10](=[S:12])[NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Ca+2]>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:12][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 66144Ethyl bromopyruvateHCID 5324304tert-butyl N-(carbamothioylmethyl)carbamate

Product 1

HCID 9925901Ethyl 2-{[(tert-butoxycarbonyl)amino]methyl}-1,3-thiazole-4-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10 g of the above-obtained (tert-butoxycarbonylamino)acetothioamide in 150 ml of ethanol were added 7.3 ml of ethyl bromopyruvate and 2.7 g of calcium carbonate, and the mixture was stirred at room temperature for 6 hours. The reaction solution was filtered, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in chloroform. The solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and a small amount of water, and then dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure, and isopropyl ether was added to the residue. The crystals precipitated were collected by filtration, and dried under reduced pressure to give 11.2 g (yield 74%) of ethyl 2-(tert-butoxycarbonylamino)methylthiazole-4-carboxylate.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washThe solution was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala small amount of water, and then dried over anhydrous magnesium sulfate
  6. concentrationThe resultant was concentrated under reduced pressure, and isopropyl ether
  7. additionwas added to the residue
  8. customThe crystals precipitated
  9. filtrationwere collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-2afa86fa68fb40c1a8e59c9cc6853a4d
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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