tert-butyl hydroxy(methyl)carbamate

tert-butyl hydroxy(methyl)carbamate Property

Boiling point:

60-65 °C(Press: 3 Torr)

Density 

1.083±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

9.04±0.50(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

tert-butyl hydroxy(methyl)carbamate Chemical Properties,Usage,Production

Synthesis

The general procedure for synthesizing tert-butyl hydroxy(methyl)carbamate from di-tert-butyl dicarbonate and N-methylhydroxylamine hydrochloride is as follows: 1. in a dry reaction flask, dissolve N-methylhydroxylamine hydrochloride in an appropriate amount of anhydrous organic solvent, such as dichloromethane or tetrahydrofuran. 2. An equimolar amount of di-tert-butyl dicarbonate is slowly added while the reaction mixture is stirred under cooling in an ice bath. 3. the reaction mixture was continued to be stirred at room temperature for 4-6 hours and the progress of the reaction was monitored by thin layer chromatography (TLC). 4. Upon completion of the reaction, the reaction was quenched with water and the product was extracted with an organic solvent. 5. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. 6. The crude product was purified by column chromatography to obtain the target compound tert-butyl hydroxy(methyl)carbamate. Example 4: Synthesis of NOOTA10107 containing N-methylhydroxylamine According to Scheme 4, the steps for synthesizing N-methylhydroxylamine-containing NOOTA linker are as follows: 1. in accordance with the general steps described above, tert-butyl hydroxy(methyl)carbamate was synthesized from di-tert-butyl dicarbonate and N-methylhydroxylamine hydrochloride. 2. the obtained tert-butyl hydroxy(methyl)carbamate is further reacted with the precursor compound of NOTA linker, and the specific reaction conditions and steps are to be adjusted according to the structure and requirements of NOTA linker. 3. After completion of the reaction, the NOTA linker containing N-methylhydroxylamine is purified by an appropriate purification method, such as column chromatography or recrystallization.

References

[1] Journal of the American Chemical Society, 2013, vol. 135, # 31, p. 11521 - 11524
[2] Organic Letters, 2005, vol. 7, # 25, p. 5729 - 5732
[3] Organic Letters, 2007, vol. 9, # 20, p. 4009 - 4012
[4] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 4, p. 1221 - 1224
[5] Organic Letters, 2009, vol. 11, # 22, p. 5210 - 5213