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Chemical Structure| 372-75-8 Chemical Structure| 372-75-8
Chemical Structure| 372-75-8

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H-Cit-OH is a natural product isolated and purified from the herbs of Citrullus lanatus.

Synonyms: N5-Carbamoyl Ornithine; NSC 27425; delta-Ureidonorvaline

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Product Details of L-Citrulline

CAS No. :372-75-8
Formula : C6H13N3O3
M.W : 175.19
SMILES Code : N[C@@H](CCCNC(N)=O)C(O)=O
Synonyms :
N5-Carbamoyl Ornithine; NSC 27425; delta-Ureidonorvaline
MDL No. :MFCD00064397
InChI Key :RHGKLRLOHDJJDR-BYPYZUCNSA-N
Pubchem ID :9750

Safety of L-Citrulline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of L-Citrulline

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 372-75-8 ]
  • Downstream synthetic route of [ 372-75-8 ]

[ 372-75-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 372-75-8 ]
  • [ 2937-50-0 ]
  • [ 6298-03-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With copper (II) carbonate hydroxide In water for 0.5 h; Reflux
Stage #2: With sodium carbonate In water at 0 - 20℃; for 12 h;
Stage #3: With thioacetamide In water at 50℃; for 3 h;
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: [1] Patent: WO2015/95227, 2015, A2, . Location in patent: Page/Page column 168; 169.
 

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