Reaktion #473880

Reaktionsgleichung

1-[(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-methyl]-cyclobutanecarboxylic acid tert-butyl ester

1-[(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-methyl]-cyclobutanecarboxylic acid tert-butyl ester

dioxane

→

title product

1-[(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-methyl]-cyclobutanecarboxylic acid

Lösungsmittel

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between water and EtOAc
2. 2
   workup.ADDITIONthe pH of the aqueous portion was adjusted to 14 by addition of 2N NaOH
3. 3
   WaschenThe basic aqueous solution was washed with EtOAc
4. 4
   Einengenconcentrated in vacuo
5. 5
   workup.ADDITIONthe pH was adjusted to 6 by dropwise addition of 2N HCl
6. 6
   FiltrationThe resulting solid was filtered
7. 7
   Waschenwashed with water (20 ml), diethyl ether (20 ml)
8. 8
   Sonstigedried under vacuum at 50° C.

Vorschrift

A suspension of 1-[(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-methyl]-cyclobutanecarboxylic acid tert-butyl ester (step 1) (730 mg, 1.080 mmol) in 4N HCl in dioxane (10 ml, 40.0 mmol) was stirred at RT for 1 h. The reaction mixture was partitioned between water and EtOAc and the pH of the aqueous portion was adjusted to 14 by addition of 2N NaOH. The basic aqueous solution was washed with EtOAc and concentrated in vacuo. The dry residue was slurried in water and the pH was adjusted to 6 by dropwise addition of 2N HCl. The resulting solid was filtered and washed with water (20 ml), diethyl ether (20 ml) and dried under vacuum at 50° C. to afford the title product; LC-MS Rt 2.29 mins; 620.3 [M+H]+, Method 10minLC_v003.

Quelle