1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& Chemical Properties

Melting point:

83-88 °C(lit.)

Boiling point:

308.6±44.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

InChI

InChI=1S/C10H17NO5Si/c1-17(2,3)7-6-15-10(14)16-11-8(12)4-5-9(11)13/h4-7H2,1-3H3

InChIKey

FLDNDAMSCINJDX-UHFFFAOYSA-N

SMILES

C(OCC[Si](C)(C)C)(=O)ON1C(=O)CCC1=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2931.90.9010

1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)& Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

1-[2-(Trimethylsilyl)ethoxycarbonyloxy]pyrrolidin-2,5-dione (Teoc-OSu) may be used as an acylating reagent to produce Teoc-amino acid derivatives.

General Description

1-[2-(Trimethylsilyl)ethoxycarbonyloxy]pyrrolidin-2,5-dione (Teoc-OSu) is a silicon-based reagent that can be prepared from 2-trimethylsilylethyl carbonochloridite and N-hydroxysuccinimide.

Synthesis

2-(Trimethylsilyl)ethyl chloroformate (S13) was dissolved in acetonitrile (105 mL) at 0 °C. Subsequently, N-hydroxybutanediimide (5.22 g, 45.4 mmol, 1.30 eq.) and triethylamine (4.59 g, 45.4 mmol, 1.30 eq.; dissolved in 11.0 mL acetonitrile) were added to the solution. The reaction mixture was kept stirred at 0 °C for 16 hours. After completion of the reaction, the mixture was poured into water. The aqueous layer was extracted with ether (6 times). The organic layers were combined and washed sequentially with water (2 times), 1.0 M hydrochloric acid and then with water, followed by drying with magnesium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give 1-[2-(trimethylmethylsilyl)ethoxycarbonyloxy]pyrrolidine-2,5-dione (S14, 7.72 g, 29.8 mmol, 85% yield in two steps) as a colorless solid.

References

[1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 564 - 570
[2] Synthesis, 1987, # 4, p. 346 - 349
[3] Patent: US6627660, 2003, B1
[4] Patent: US2004/116391, 2004, A1

1-(2-(TRIMETHYLSILYL)ETHOXYCARBONYLOXY)&(78269-85-9)Related Product Information

• 1-[(2-TRIMETHYLSILYL)ETHOXYCARBONYLOXY]PYRROLIDIN-2,5-DIONE
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