(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID Chemical Properties

Melting point:

152.9 °C

Boiling point:

368.97°C (rough estimate)

Density 

1.1781 (rough estimate)

refractive index 

1.5718 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

4.31±0.40(Predicted)

Appearance

White to off-white Solid

optical activity

[α]20/D -48,5±2°, c =1% in methanol

Major Application

peptide synthesis

InChI

InChI=1S/C11H17NO4/c1-11(2,3)16-10(15)12-8-5-4-7(6-8)9(13)14/h4-5,7-8H,6H2,1-3H3,(H,12,15)(H,13,14)/t7-,8+/m1/s1

InChIKey

WOUNTSATDZJBLP-SFYZADRCSA-N

SMILES

[C@H]1(C(O)=O)C[C@@H](NC(OC(C)(C)C)=O)C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

HazardClass 

IRRITANT

HS Code 

29223900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID Usage And Synthesis

Chemical Properties

beige to light brown crystalline powder

Uses

peptide synthesis

Synthesis

To a (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (5.0 g, 46 mmol)/water (30.5 ml) solution of Aqueous HCl solution (2M, 23.0 ml, 46.0 mmol) was added to the solution. The reaction mixture was heated at about 80 ??C for about 2 h to . After heating at about 80 ??C for about 2 h to , the reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. The solid was dried in a vacuum oven at about 70 ??C and used without further purification. The solvent was added to (1S,4R)-4-amino at about 0??C. The solvent was removed under pressure. (1S,4R)-4-amino -cyclopent-2-enecarboxylic acid hydrochloride (9.20 g, 45.8 mmol)/1,4-dioxane (15 ml) and water (18.3 ml). (18.3 ml) solution was added DIEA (32.0 ml, 183 mmol). After stirring for about 5 minutes, di-tert-butyl bicarbonate (di-tert-butyl ) was added. dicarbonate) (11.7 ml, 50.4 mmol)/1,4-dioxane hexane (5 ml) solution. The reaction mixture was brought to ambient temperature and stirred for about 18 hours. The solvent was removed under reduced pressure and the crude oil was dried in a vacuum oven at about 65??C for about 3 hours. The crude oil was extracted with A gradient elution of 80-100% EtOAc/heptane purified the crude product by silica gel chromatography to afford (-)-(1S,4R)-N-tert-butyloxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid (5.2 g, 50%, two steps): LC/MS (Table 2, method a) Rt = 1.81 min; MS m/z: 226(M-H)-.

(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID(151907-79-8)Related Product Information

• (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• (+)-(1S,3R)-N-BOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID
• BOC-1,3-CIS-ACHC-OH
• (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI)
• (-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• (1S-cis)-4-Amino-2-cyclopentene-1-methanol
• 2-Cyclopentene-1-carboxylicacid,4-amino-
• (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• 1-N-BOC-AMINO-2-CYCLOPENTENE
• Carbamic acid, 4-pentenyl-, 1,1-dimethylethyl ester (9CI)
• CARBAMIC ACID, [4(S)-(HYDROXYMETHYL)-2-CYCLOPENTEN-1-YL]-1,1-DIMETHYLETHYL ESTER, (1R-CIS)-
• TERT-BUTYL N-ALLYLCARBAMATE
• VIGABATRIN