H-LYS(ALLOC)-OH synthesis
- Product Name:H-LYS(ALLOC)-OH
- CAS Number:6298-03-9
- Molecular formula:C10H18N2O4
- Molecular Weight:230.26
372-75-8
2937-50-0
6298-03-9
Step 5. A mixed solution of L-citrulline (10 g, 68.4 mmol) and basic copper carbonate (15.12 g, 68.4 mmol) in distilled water (100 mL) was heated to reflux for 30 minutes. Solids generated during refluxing were removed by thermal filtration. The filtrate was cooled to 0 °C and the pH was adjusted to 9 by addition of anhydrous sodium carbonate (1.0 g). allyl chloroformate (10.8 mL, 102.6 mmol) was added slowly and dropwise while stirring at 0 °C. During dropwise addition, the pH of the reaction mixture was maintained at 9 by addition of anhydrous sodium carbonate (20 g). the reaction mixture was gradually warmed up to room temperature with continuous stirring for 12 h. The reaction was carried out by filtration. Upon completion of the reaction, the resulting blue solid product was quantitatively collected by filtration. The resulting copper salt solid of Orn (Alloc) was suspended in distilled water (200 mL) and thioacetamide (6.511 g, 86.66 mmol, 2 equiv) was added. The basic suspension was stirred at 50 °C for 3 h, during which time the solid gradually dissolved. Subsequently, the solution was acidified to pH 2 with 2 M hydrochloric acid and boiling was continued for 5 min. The resulting copper sulfide precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to about 100 mL, at which point the hydrochloride product of Orn (Alloc) precipitated quantitatively as a white solid.
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6298-03-9
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Yield: 100%
Reaction Conditions:
Stage #1:Citrulline with copper (II) carbonate hydroxide in water for 0.5 h;Reflux;
Stage #2:Allyl chloroformate with sodium carbonate in water; pH=9 at 0 - 20; for 12 h;
Stage #3: with thioacetamide in water at 50; for 3 h;Temperature;Time;
Steps:
58.5 Step 5
Step 5.
A solution of 58-7 (10 g, 68.4 mmol) and Cu(OH)2C03 (15.12 g, 68.4 mmol) in H20 (100 mL) was heated at reflux for 30 min. Solids formed during reflux were removed by filtration while hot. The filtrate was cooled to 0°C and was adjusted to pH 9 by addition of solid Na2C03 (1.0 g). AllocCl (10.8 mL, 102.6 mmol) was added dropwise, while the solution stirred at 0°C. During the addition, the reaction mixture was maintained at pH 9 by the addition of solid Na2C03 (20 g). The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The blue solid product formed during the reaction was collected by filtration in quantitative yield. The solid copper salt of Orn( Alloc) collected above was suspended in H20 (200 mL) and two equivalents of thioacetamide (6.511 g, 86.66 mmol) were added to. The alkaline suspension was stirred at 50°C for 3 h, during which time, the solid slowly dissolved. The solution was then acidified to pH 2 with 2M HC1 and was further boiled for 5 min. The precipitated CuS was removed by filtration. The filtrate was concentrated under vacuum to about 100 mL, at which point the product hydrochloride salt of Orn(Alloc) 58-8 precipitated as a white solid in quantitative yield.
References:
GENENTECH, INC.;THE UNIVERSITY OF AUCKLAND;LEE, Ho Huat;TERCEL, Moana;FLYGARE, John A.;GUNZNER-TOSTE, Janet;PILLOW, Thomas H.;SAFINA, Brian;STABEN, Leanna;VERMA, Vishal;WEI, BinQing;ZHAO, Guiling WO2015/95227, 2015, A2 Location in patent:Page/Page column 168; 169
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6298-03-9
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