N-Boc-4-oxo-L-Proline methyl ester Chemical Properties

Melting point:

35-40°C

alpha 

14 º (C=1 IN CHLOROFORM)

Boiling point:

333.1±42.0 °C(Predicted)

Density 

1.209±0.06 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

-20°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

-3.86±0.40(Predicted)

Appearance

Light yellow to brown Solid

optical activity

[α]22/D +14.0°, c = 1 in chloroform

InChI

InChI=1S/C11H17NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h8H,5-6H2,1-4H3/t8-/m0/s1

InChIKey

UPBHYYJZVWZCOZ-QMMMGPOBSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(=O)C[C@H]1C(OC)=O

CAS DataBase Reference

102195-80-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-41

Safety Statements 

26-36/37-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

N-Boc-4-oxo-L-Proline methyl ester Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

(2S)-1-Boc-4-oxo-proline Methyl Ester (cas# 102195-80-2) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of BOC-4-oxo-L-proline methyl ester from N-Boc-trans-4-hydroxy-L-proline methyl ester: (a) To a solution of methyl (2S,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate (40 g, 157 mmol) in dichloromethane (DCM, 500 mL) was added Days-Martin oxidizer (DMP, 80 g, 189 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 4 h. Upon completion of the reaction, the reaction was quenched with sodium bisulfite (NaHSO3) solution. The reaction mixture was extracted with dichloromethane (DCM) and the organic phase was washed with aqueous sodium bicarbonate (NaHCO3) solution. Concentration of the organic phase afforded the title intermediate (2S)-1-tert-butoxycarbonyl-4-oxopyrrolidine-2-carboxylic acid methyl ester (33 g, 89% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ (ppm) 1.51 (s, 9H), 2.550-2.597 (d, 1H, J = 18.8Hz), 2.876-2.944 (t, 1H, J = 13.6Hz), 3.895 (s, 3H), 3.766-3.895 (m, 1H), 4.696- 4.814 (m, 1H).

References

[1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 5, p. 740 - 742
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1557 - 1572
[3] Journal of the American Chemical Society, 2016, vol. 138, # 7, p. 2443 - 2453
[4] Angewandte Chemie - International Edition, 2002, vol. 41, # 9, p. 1600 - 1602
[5] Tetrahedron Letters, 2003, vol. 44, # 42, p. 7809 - 7812

N-Boc-4-oxo-L-Proline methyl ester(102195-80-2)Related Product Information

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