BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER Chemical Properties

Melting point:

64-67°C

Boiling point:

366.7±42.0 °C(Predicted)

Density 

1.138±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-3.86±0.40(Predicted)

color 

White to off-white

optical activity

10.2°(C=1g/100ml CHCL3)

InChI

InChI=1S/C14H23NO5/c1-13(2,3)19-11(17)10-7-9(16)8-15(10)12(18)20-14(4,5)6/h10H,7-8H2,1-6H3/t10-/m0/s1

InChIKey

MPNWQUWKRDADHK-JTQLQIEISA-N

SMILES

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

LogP

2.62

Safety Information

HS Code 

2933998090

BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER Usage And Synthesis

Synthesis

For the synthesis of di-tert-butyl (S)-4-oxopyrrolidine-1,2-dicarboxylate (16c), (S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (16b, 1.35 g, 5.9 mmol) was dissolved in anhydrous dichloromethane (27 mL) and the solution was cooled to 0 °C. Subsequently, tert-butanol (1.7 mL, 17.7 mmol) and 4-dimethylaminopyridine (DMAP, 72 mg, 0.59 mmol) were sequentially added to the solution. After stirring for 5 min, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl, 1.19 g, 6.2 mmol) was added. The reaction mixture was gradually warmed to room temperature and continued to stir overnight. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution and extracted three times with dichloromethane. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was removed by concentration under reduced pressure and the resulting residue was purified by fast column chromatography (eluent: n-hexane/ethyl acetate, 8:1) to afford the target product 16c (0.96 g, 57% yield) as a light yellow oil.

References

[1] Tetrahedron, 1995, vol. 51, # 14, p. 4195 - 4212
[2] Patent: WO2017/53990, 2017, A1. Location in patent: Paragraph 00150

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