Boc-L-beta-Homoproline

Bezeichnung:Boc-L-beta-Homoproline

CAS-Nr56502-01-3

Englisch Name:Boc-L-beta-Homoproline

CBNumberCB5169171

SummenformelC11H19NO4

Molgewicht229.27

MOL-Datei56502-01-3.mol

Boc-L-beta-Homoproline physikalisch-chemischer Eigenschaften

Schmelzpunkt	98 °C
Siedepunkt	357.4±15.0 °C(Predicted)
Dichte	1.151±0.06 g/cm3(Predicted)
storage temp.	2-8°C
pka	4.56±0.10(Predicted)
Aggregatzustand	Crystalline Powder
Farbe	White to off-white
BRN	478306
Major Application	peptide synthesis
InChI	InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-5-8(12)7-9(13)14/h8H,4-7H2,1-3H3,(H,13,14)/t8-/m0/s1
InChIKey	GDWKIRLZWQQMIE-QMMMGPOBSA-N
SMILES	N1(C(OC(C)(C)C)=O)CCC[C@H]1CC(O)=O
CAS Datenbank	56502-01-3(CAS DataBase Reference)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
HazardClass	IRRITANT
HS Code	29339900
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

Boc-L-beta-Homoproline Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
Building block for necine alkaloids.
Verwenden
Boc-L-beta-homoproline is an amino acid derivative which is a reagent in the synthesis of dihydroisoxazole inhbitors of human transglutaminase 2, an enzyme that catalyzes the modification of glutamine residues. This enzyme has been implicated in numerous inflmmatory, fibrotic and other diseases.
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthese

88790-37-8

56502-01-3

General procedure for the synthesis of (S)-2-(2-pyrrolidinyl)acetic acid from methyl (S)-2-(2-pyrrolidinyl)acetate: tert-butyl (2S)-2-(2-methoxy-2-oxoethyl)-1-pyrrolidinecarboxylate (8.35 g, 34.3 mmol) was dissolved in 150 mL of methanol. 50 mL of 1 M aqueous sodium hydroxide solution was added and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solution was concentrated under reduced pressure to about 100 mL. The concentrated solution was added to 300 mL of water and extracted twice with ether (2 x 100 mL). The aqueous phase was acidified to pH 2 with 12N hydrochloric acid and extracted with ether twice more (2 x 100 mL). The aqueous layer was saturated with saturated sodium chloride solution and then extracted with ether a third time (100 mL). All organic layers were combined, washed sequentially with water and saturated sodium chloride solution, and then dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to afford the title compound (S)-2-(1-tert-butoxycarbonyl-2-pyrrolidinyl)acetic acid as a white solid (7.28 g, 31.7 mmol, 92.6% yield). peaks, 4H), 1.48 (single peak, 9H) ppm.
Einzelnachweise
[1] Patent: WO2003/76440, 2003, A1. Location in patent: Page/Page column 140
[2] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8730 - 8733
[3] Organic and Biomolecular Chemistry, 2003, vol. 1, # 22, p. 3977 - 3988
[4] Tetrahedron Letters, 1997, vol. 38, # 20, p. 3609 - 3610

Boc-L-beta-Homoproline Upstream-Materialien And Downstream Produkte

Boc-L-beta-Homoproline Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

56502-01-3, Boc-L-beta-Homoproline Verwandte Suche:

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