tert-Butyl-(S)-[1-[[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl]-2-methylpropyl]carbamat

Bezeichnung:tert-Butyl-(S)-[1-[[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl]-2-methylpropyl]carbamat

CAS-Nr3392-12-9

Englisch Name:tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester

CBNumberCB3363294

SummenformelC14H22N2O6

Molgewicht314.33

MOL-Datei3392-12-9.mol

Synonyma

tert-Butyl-(S)-[1-[[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl]-2-methylpropyl]carbamat

tert-Butyl-(S)-[1-[[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl]-2-methylpropyl]carbamat physikalisch-chemischer Eigenschaften

Schmelzpunkt	126-128 °C
Dichte	1.22±0.1 g/cm3(Predicted)
storage temp.	-20°C
pka	10.72±0.46(Predicted)
Aggregatzustand	Powder
Farbe	White to off-white
Optische Rotation	[α]20/D 38±1°, c = 2% in dioxane
Sensitive	Moisture Sensitive
BRN	1551859
Major Application	peptide synthesis
InChI	1S/C14H22N2O6/c1-8(2)11(15-13(20)21-14(3,4)5)12(19)22-16-9(17)6-7-10(16)18/h8,11H,6-7H2,1-5H3,(H,15,20)/t11-/m0/s1
InChIKey	POBDBYGSGKMZPH-NSHDSACASA-N
SMILES	CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O
CAS Datenbank	3392-12-9(CAS DataBase Reference)

Sicherheit

WGK Germany	3
F	3-10-21
HS Code	2933998090
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White powder
Verwenden
peptide synthesis
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthese

6066-82-6

13734-41-3

3392-12-9

Step A: Boc-L-valine (1.03 g, 4.74 mmol), N-hydroxysuccinimide (1.22 g, 10.6 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC, 1.60 g, 8.35 mmol) were sequentially added to a dry round-bottom flask. The above reagents were dissolved in anhydrous dichloromethane (30 mL), and the reaction system was sealed through a rubber septum and displaced three times with argon to exclude oxygen. Subsequently, the reaction mixture was stirred at room temperature.After 3 days, thin layer chromatography (TLC) detection (ninhydrin color development) confirmed that the Boc-L-valine was fully reacted. The reaction solution was washed sequentially with water, saturated aqueous sodium bicarbonate, and the aqueous phase was back-extracted with dichloromethane. The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and dried under vacuum to obtain white solid Boc-L-valine hydroxysuccinimide ester (1.52 g, 100% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3): δ 4.98 (broad peak, 1H), 4.58 (double peak, 1H), 2.82 (multiple peaks, 4H), 2.27 (multiple peaks, 1H), 1.44 (single peak, 9H), 1.03 (double peaks, 6H).
Einzelnachweise
[1] Patent: WO2016/160615, 2016, A1. Location in patent: Paragraph 0444; 0445
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 14, p. 2461 - 2480
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2852 - 2857
[4] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 2305 - 2308
[5] Journal of Organic Chemistry, 1986, vol. 51, # 24, p. 4580 - 4585

tert-Butoxycarbonyl-L-valine N-hydroxysuccinimide ester Upstream-Materialien And Downstream Produkte

tert-Butyl-(S)-[1-[[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl]-2-methylpropyl]carbamat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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