1-T-BOC-PIPERIDINE-4-SPIRO-5'-HYDANTOIN

1-T-BOC-PIPERIDINE-4-SPIRO-5'-HYDANTOIN Property

Melting point:

242-244°C

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Dichloromethane, DMSO, Methanol

form 

Solid

pka

10.10±0.20(Predicted)

color 

White to Off-White

InChI

InChI=1S/C12H19N3O4/c1-11(2,3)19-10(18)15-6-4-12(5-7-15)8(16)13-9(17)14-12/h4-7H2,1-3H3,(H2,13,14,16,17)

InChIKey

DHJXKTPWDXJQEK-UHFFFAOYSA-N

SMILES

N1C2(CCN(C(OC(C)(C)C)=O)CC2)C(=O)NC1=O

CAS DataBase Reference

183673-70-3

Safety

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

1-T-BOC-PIPERIDINE-4-SPIRO-5'-HYDANTOIN Chemical Properties,Usage,Production

Chemical Properties

Off-White Powder

Uses

A cyclic a,a-disubstituted amino acid for preparation of water-soluble highly helical peptides

Uses

A cyclic α,α-disubstituted amino acid for preparation of water-soluble highly helical peptides.

Synthesis

An aqueous solution (50 mL) of potassium cyanide (22.5 g, 0.335 mol) was slowly added dropwise over a period of 5 minutes to a mixture of water (90 mL) and methanol (110 mL) containing N-tert-butoxycarbonyl-4-piperidone (32.48 g, 0.1598 mol) and ammonium carbonate (33.8 g, 0.351 mol). Upon completion of the dropwise addition, an off-white precipitate rapidly appeared in the reaction mixture. Subsequently, the reaction flask was sealed and the suspension was stirred continuously at room temperature for 72 hours. Upon completion of the reaction, the light yellow precipitate was collected by filtration and washed with a small amount of water to afford 8-Boc-2,4,8-triazaspiro[4.5]decane-1,3-dione (37.1 g, 86% yield) as a colorless solid.

References

[1] Patent: WO2009/64274, 2009, A1. Location in patent: Page/Page column 15
[2] Patent: WO2007/139813, 2007, A1. Location in patent: Page/Page column 17
[3] Patent: US2005/261322, 2005, A1. Location in patent: Page/Page column 19
[4] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2687 - 2692