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

Melting point:

152°C

Boiling point:

382.3±42.0 °C(Predicted)

Density 

1.18

storage temp. 

2-8°C

pka

4.31±0.40(Predicted)

form 

Crystalline Powder

color 

Off-white

optical activity

[α]20/D +48.5±2°, c = 1% in methanol

BRN 

6177417

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+/m0/s1

InChIKey

WOUNTSATDZJBLP-JGVFFNPUSA-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

MSDS

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

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

Chemical Properties

off-white crystalline powder

Synthesis

(1R,4S)-4-Aminocyclopent-2-ene-1-carboxylic acid (130 g, 1.0 mol) was dissolved in a solvent mixture of water (250 mL) and THF (750 mL) and sodium bicarbonate (170 g, 2.0 mol) was added. After stirring for 30 minutes, solid di-tert-butyl dicarbonate (230 g, 1.05 mol) was slowly added. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the insoluble material was removed by filtration and THF was removed by evaporation.The residue was cooled to 0 °C and the pH was adjusted to 3 by slow addition of aqueous 2N HCl (ca. 500 mL).The precipitated white solid was collected by filtration, washed with water, and dried under vacuum overnight to afford (1R,4S)-4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid (230 g, 100%). The product was characterized by 1H NMR (400 MHz, CD3OD): δ 5.95 (m, 1H), 5.79 (m, 1H), 4.80 (br s, 1H), 3.45 (m, 1H), 2.50 (m, 1H), 1.79 (m, 1H), 1.44 (s, 9H).

References

[1] Patent: WO2004/76411, 2004, A2. Location in patent: Page 27-28
[2] Patent: WO2003/93231, 2003, A2. Location in patent: Page/Page column 55-56
[3] Patent: US2007/155731, 2007, A1. Location in patent: Page/Page column 27
[4] Patent: US2007/155731, 2007, A1. Location in patent: Page/Page column 35
[5] Patent: WO2005/110409, 2005, A2. Location in patent: Page/Page column 30

(+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID(151907-80-1)Related Product Information

• Trans-(1S,4S)-4-Boc-aMino-2-Cyclopentene-1-carboxylic acid Methyl ester
• Trans-(1R,4R)-4-Boc-aMino-2-Cyclopentene-1-carboxylic acid Methyl ester
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• (1R,3S)-3-Aminocyclopentanecarboxylic acid
• (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID