Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Melting point:

86-87℃

Boiling point:

249℃

Density 

1.015

Flash point:

104℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

11.43±0.46(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C8H15NO3/c1-6(5-10)9-7(11)12-8(2,3)4/h5-6H,1-4H3,(H,9,11)/t6-/m1/s1

InChIKey

OEQRZPWMXXJEKU-ZCFIWIBFSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@H](C)C=O

Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Synthesis

The general procedure for the synthesis of (R)-2-(tert-butoxycarbonylamino)propanal from N-Boc-L-alaninol was as follows: to a solution of oxalyl chloride (3.1 g, 24.5 mmol) in anhydrous dichloromethane (DCM, 200 mL) was slowly added dimethylsulfoxide (DMSO, 2.9 mL, 40.8 mmol) at -60 °C. The reaction mixture was stirred at this temperature for 30 minutes. Subsequently, a solution of tert-butyl (R)-(1-hydroxypropan-2-yl)carbamate (3.5 g, 20 mmol) in dichloromethane (DCM, 20 mL) was slowly added at -60 °C. The resulting solution continued to be stirred at -60°C for 30 minutes. Next, triethylamine (11.1 mL, 80 mmol) was added at -60 °C and the reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, water (100 mL) was added for quenching and the mixture was extracted with dichloromethane (3 x 50 mL). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4), and the filtrate was filtered and concentrated to afford the target product (R)-2-(tert-butoxycarbonylamino)propanal (aldehyde 322) as a light yellow oil (3.2 g, 94% yield), which could be used in the subsequent steps without further purification.

References

[1] Chemistry - An Asian Journal, 2012, vol. 7, # 7, p. 1542 - 1545
[2] Patent: US2015/374858, 2015, A1. Location in patent: Paragraph 0500
[3] Patent: US2009/5359, 2009, A1. Location in patent: Page/Page column 42
[4] Patent: US2009/36419, 2009, A1. Location in patent: Page/Page column 87
[5] Patent: WO2012/125887, 2012, A1. Location in patent: Page/Page column 173