MORPHOLIN-4-YL-ACETIC ACID Chemical Properties

Melting point:

160-161℃

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

White

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C6H11NO3/c8-6(9)5-7-1-3-10-4-2-7/h1-5H2,(H,8,9)

InChIKey

ICGYBJNONRDZOP-UHFFFAOYSA-N

SMILES

C(O)(=O)CN1CCOCC1

CAS DataBase Reference

89531-58-8

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MORPHOLIN-4-YL-ACETIC ACID Usage And Synthesis

Uses

4-Morpholineacetic Acid Hydrochloride is an intermediate of Carfilzomib (C183460) which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Chemical Properties

White solid

Uses

4-Morpholineacetic Acid Hydrochloride is an intermediate of Carfilzomib (C183460) which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Synthesis

The general procedure for the synthesis of morpholine-4-acetic acid hydrochloride from ethyl 2-(4-morpholinyl)acetate is as follows: ethyl 4-morpholinoacetate (1.1 g, 6.3 mmol) was added to 3M hydrochloric acid solution (35 ml) and the reaction was carried out at reflux for 2 hours. After completion of the reaction, the mixture was stirred at room temperature for 24 hours. Subsequently, the reaction solution was concentrated under reduced pressure. The obtained residue was dissolved in methanol and concentrated again under reduced pressure. The final solid product obtained was suspended in ether, separated by filtration and dried under reduced pressure to give 1.05 g of morpholine-4-acetic acid hydrochloride in 91.7% yield. The product was characterized by NMR (DMSO-d6) with chemical shifts of 3.3 (s, 4H), 3.9 (s, 4H), 4.2 (s, 2H).

References

[1] Journal of the American Chemical Society, 2017, vol. 139, # 34, p. 11895 - 11902
[2] Patent: US6352993, 2002, B1. Location in patent: Page column 13
[3] Journal of Molecular Structure, 2001, vol. 560, # 1-3, p. 261 - 273
[4] Patent: US5521179, 1996, A
[5] Bioconjugate Chemistry, 2016, vol. 27, # 1, p. 226 - 237

MORPHOLIN-4-YL-ACETIC ACID(89531-58-8)Related Product Information

• MORPHOLIN-2-YL-ACETIC ACID ETHYL ESTER
• MORPHOLIN-4-YL-ACETIC ACID
• MORPHOLIN-3-YL-ACETIC ACID ETHYL ESTER HYDROCHLORIDE
• (S)-Morpholin-3-yl-acetic acid
• (4-BENZYL-MORPHOLIN-2-YL)-ACETIC ACID HYDROCHLORIDE
• MORPHOLIN-3-YL-ACETIC ACID HYDROCHLORIDE
• MORPHOLIN-3-YL-ACETIC ACID METHYL ESTER
• (4-BENZYL-MORPHOLIN-2-YL)-ACETIC ACID METHYL ESTER
• (2R,6S)-(2,6-DIMETHYL-MORPHOLIN-4-YL)-ACETIC ACID
• (R)-(4-BENZYL-MORPHOLIN-3-YL)-ACETIC ACID METHYL ESTER,(R)-(4-Benzyl-morpholin-3-yl)-acetic acid methyl
• MORPHOLIN-2-YL-ACETIC ACID
• (4-Benzyl-morpholin-3-yl)-acetic acid methyl ester
• (5,5-DIMETHYL-MORPHOLIN-2-YL)-ACETIC ACID
• 2-(4-N-CBZ-MORPHOLIN-2-YL)ACETIC ACID
• (4-BENZYL-MORPHOLIN-2-YL)-ACETIC ACID
• (4-METHOXY-PHENYL)-MORPHOLIN-4-YL-ACETIC ACID HYDROCHLORIDE
• (2-OXO-MORPHOLIN-4-YL)-ACETIC ACID
• 2-(4-N-FMOC-MORPHOLIN-2-YL)ACETIC ACID