1-(Cbz-amino)cyclopropanecarboxylic acid Chemical Properties

Melting point:

157.0 to 161.0 °C

Boiling point:

449.0±34.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.02±0.20(Predicted)

color 

White to Almost white

CAS DataBase Reference

84677-06-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2924297099

MSDS

• Language:English Provider:SigmaAldrich

1-(Cbz-amino)cyclopropanecarboxylic acid Usage And Synthesis

Chemical Properties

White powder

Uses

1-(Benzyloxycarbonylamino)cyclopropyl-1-carboxylic Acid is a useful intermediate used in the preparation of the analogs of vasopressins and other peptide derivatives.

Synthesis

Step A: Synthesis of intermediate VI A tetrahydrofuran (THF, 500 mL) solution of benzyl 2,5-dioxopyrrolidin-1-yl carbonate (83 g, 334 mmol) was added slowly and dropwise to an aqueous (500 mL) solution of 1-aminocyclopropanecarboxylic acid (25 g, 247 mmol). A solution of sodium bicarbonate (91 g, 1088 mmol) in water (500 mL) was added dropwise to the reaction mixture under cooling in an ice bath. After the dropwise addition, the reaction system was slowly warmed to room temperature and the reaction was continued with stirring for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was resuspended in dichloromethane (200 mL) and extracted with water (500 mL). The aqueous phase was acidified by acetic acid and the precipitated white solid was collected by filtration to afford 1-((benzyloxy)carbonyl)amino)cyclopropanecarboxylic acid (53 g, 171 mmol, 69.2% yield). The crude product can be directly used in the next step of the reaction.LC/MS analysis result: m/z calculated value 235.1, measured value 258.0 ([M+Na]+).

References

[1] Synlett, 2004, # 14, p. 2489 - 2492
[2] Patent: WO2013/20245, 2013, A1. Location in patent: Paragraph 00105
[3] Patent: WO2015/95227, 2015, A2. Location in patent: Page/Page column 220; 221

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