ChemicalBook CAS DataBase List N-CARBAMYL-L-GLUTAMIC ACID

N-CARBAMYL-L-GLUTAMIC ACID synthesis

4synthesis methods

Product Name:N-CARBAMYL-L-GLUTAMIC ACID
CAS Number:1188-38-1
Molecular formula:C6H10N2O5
Molecular Weight:190.15

Carglumic acid is an orphan drug, marketed by Orphan Europe under the trade name Carbaglu. Carglumic acid is used for the treatment of hyperammonaemia in patients with N-acetylglutamate synthase deficiency. The initial daily dose ranges from 100 to 250 mg/kg, adjusted thereafter to maintain normal plasma levels of ammonia.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

Verardo, Giancarlo; Geatti, Paola; Strazzolini, Paolo Synthetic Communications Volume 37 Issue 11 Pages 1833-1844 Journal 2007

56-86-0 Synthesis

56-86-0
821 suppliers
$5.00/25g

917-61-3 Synthesis

917-61-3
298 suppliers
$14.30/5g

1188-38-1
233 suppliers
$22.00/5g

Yield:1188-38-1 91.7%

Reaction Conditions:

with lithium hydroxide monohydrate in water at 30; for 24 h;Reagent/catalyst;

Steps:

1; 4-8 Example 1 (Scheme 2 step a)
57.1 g (1.36 moles) of lithium hydroxide monohydrate is added to a reactor containing 1.2 L of water. After complete dissolution, 88.4 g (1.36 moles) of sodium cyanate is added, followed by 200 g (1.36 moles) of L-glutamic acid, and the mixture is stirred at 30°C for 24 h. 30% by weight of aqueous HC1 is then added until a pH value below 3 is reached, at which point precipitation of the product is observed. The filtered solid is washed with water (3 x 30 mL) and dried under vacuum at 50°C for 24 h. 237 g of carglumic acid is obtained (yield 91.7%), with an HPLC purity of 99.86%. (0030) The percentage of L-pyroglutamic acid in the reaction mixture after 24 h is 1.06%.

References:

PROCOS S.P.A.;MORANA, Fabio;GRANDE, Vincenzo;GOBBATO, Stefano;ROLETTO, Jacopo;PAISSONI, Paolo WO2020/75082, 2020, A1 Location in patent:Page/Page column 6-8

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590-28-3 Synthesis