1-BOC-D-PYROGLUTAMIC ACID ETHYL ESTER Chemical Properties

Melting point:

54.0 to 58.0 °C

Boiling point:

375.0±35.0 °C(Predicted)

Density 

1.182±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

-4.15±0.40(Predicted)

color 

White to Almost white

optical activity

Consistent with structure

InChI

InChI=1S/C12H19NO5/c1-5-17-10(15)8-6-7-9(14)13(8)11(16)18-12(2,3)4/h8H,5-7H2,1-4H3/t8-/m1/s1

InChIKey

YWWWGFSJHCFVOW-MRVPVSSYSA-N

SMILES

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

Safety Information

HS Code 

2933.79.8500

1-BOC-D-PYROGLUTAMIC ACID ETHYL ESTER Usage And Synthesis

Uses

1-Boc-D-Pyroglutamic acid ethyl ester is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research. It could synthesise (2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid.

Synthesis

An acetonitrile (150 mL) solution of di-tert-butyl dicarbonate (30.5 g, 0.14 mol) was slowly added to a reaction vial containing ethyl (S)-5-oxopyrrolidine-2-carboxylate (20 g, 0.127 mol) and di-tert-butyl dicarbonate (30.5 g, 0.14 mol) at 0 °C. 0.013 mol) in a reaction vial. The reaction mixture was stirred overnight at room temperature and then concentrated under vacuum. The residue was purified by fast chromatography (eluent: 30% ethyl acetate/hexane) to afford ethyl Boc-D-pyroglutamate (163A, 32.5 g, 100%) as an oil.1H NMR (CDCl3, 400 MHz) δ 4.58 (1H, dd, J = 3.0,9.5Hz), 4.22 (2H, q, J = 7.3Hz), 4.22 (2H, q, J = 7.3Hz), 4.22 (2H, q, J = 7.3Hz), 2.56-2.66 (2H, q, J = 7.3Hz). 2.56-2.66 (1H, m), 2.48 (1H, ddd, J = 3.8,9.6,13.1Hz), 2.25-2.35 (1H, m), 1.97-2.04 (1H, m), 1.48 (9H, s) and 1.28 (3H, t, J = 7.3Hz).

References

[1] Patent: US2008/9497, 2008, A1. Location in patent: Page/Page column 70-71
[2] Patent: EP2272825, 2015, B1. Location in patent: Paragraph 0138; 0139
[3] Organic Preparations and Procedures International, 2001, vol. 33, # 4, p. 405 - 409
[4] Organic and Biomolecular Chemistry, 2006, vol. 4, # 21, p. 3894 - 3897
[5] Patent: US2011/34438, 2011, A1. Location in patent: Page/Page column 25-26

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