BOC-D-NVA-OH Chemical Properties

Boiling point:

348.3±25.0 °C(Predicted)

Density 

1.081±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

Powder

pka

4.02±0.20(Predicted)

color 

White

BRN 

5260625

CAS DataBase Reference

57521-85-4(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29241990

BOC-D-NVA-OH Usage And Synthesis

Chemical Properties

Clear colorless viscid liquid

Uses

BOC-D-NVA-OH is a chemical reagent used in the preparation of benzothiophene inhibitors of MK2. Also has been used to synthesize pyrrolidine diketopiperazines to inhibit melanoma

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of (R)-2-((tert-butylcarbonyl)amino)pentanoic acid from D-norvaline and di-tert-butyl dicarbonate: (R)-2-aminopentanoic acid (2.343 g) and Na2CO3 (2.120 g) were dissolved in water (60.00 mL) to form a mixture. A solution of THF (20 mL) in Boc2O (4.88 mL) was added slowly and dropwise to the mixture at room temperature. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was washed with ether (2 × 20 mL), followed by adjusting the pH of the aqueous phase with K2SO4 solution to 3. The aqueous phase was extracted with EtOAc (2 × 30 mL), the organic phases were combined, and the solvents were evaporated after drying to give (R)-2-((tert-butylcarbonyl)amino)pentanoic acid (4 g) as a viscous oil product. Mass spectrometry (ESI) analysis showed that the theoretical molecular weight of C10H19NO4 was 217; the measured value was 216 [M-H].

References

[1] Patent: US5206235, 1993, A
[2] Patent: WO2015/180612, 2015, A1. Location in patent: Page/Page column 70

BOC-D-NVA-OH(57521-85-4)Related Product Information

• BOC-GLN-ONP
• Boc-D-Glutamine
• Nα-Boc-Nω-nitro-D-arginine
• N-Boc-N'-(2-chlorobenzyloxycarbonyl)-L-lysine
• Boc-D-Glu-OBzl
• BOC-D-LEU-OH H2O
• BOC-D-NLE-OH
• Boc-D-isoleucine
• (3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid
• BOC-D-Leucine monohydrate
• BOC-D-ORN(Z)-OH
• BOC-D-Arg(Tos)-OH
• BOC-D-PRO-OSU
• Boc-D-homophenylalanine
• Boc-L-Glutamic acid 1-benzyl ester
• BOC-L-NVA-OH
• D(-)-Norvaline
• L-Norvaline