Boc-L-beta-Homoproline Chemical Properties

Melting point:

98 °C

Boiling point:

357.4±15.0 °C(Predicted)

Density 

1.151±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.56±0.10(Predicted)

form 

Crystalline Powder

color 

White to off-white

BRN 

478306

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 DataBase Reference

56502-01-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

Boc-L-beta-Homoproline Usage And Synthesis

Uses

Building block for necine alkaloids.

Uses

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

Synthesis

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.

References

[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(56502-01-3)Related Product Information

• L-PROLINE-(4-3H(N))
• Povidone iodine
• cis-4-Hydroxy-L-proline
• tert-Butanol
• BOC-L-Proline
• N-Methyl-2-pyrrolidone
• Polyvinylpyrrolidone
• N-Vinyl-2-pyrrolidone
• Ethyl 2-(Chlorosulfonyl)acetate
• Ascoric Acid
• Acetic anhydride
• Phenylacetic acid
• METHYL-2-PYRROLIDONE
• Carbonyl iron powder
• BOC-D-BETA-HOMOPROLINE
• 3-TERT-BUTOXYCARBONYLAMINO-HEXANOIC ACID
• (S)-(1-Boc-5-oxo-pyrrolidin-2-yl)acetic acid
• (S)-2-(2-PYRROLIDINYL)ACETIC ACID