Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI)
- Product Name
- Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI)
- CAS No.
- 82353-56-8
- Chemical Name
- Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI)
- Synonyms
- tert-butyl (R)-(1-oxopropan-2-yl)carbamate;Boc-D-Ala-al;Boc-D-alaninal;N-Boc-D-Alaninal;Boc-D-Ala-aldehyde;Boc-D-propanemaldehyde;N-tert-Butoxycarbonyl-D-alaninal;(R)-2-(tert-Butoxycarbonylamino)propanal;(R)-tert-Butyl (1-oxopropan-2-yl)carbamate;tert-butyl N-[(2R)-1-oxopropan-2-yl]carbamate
- CBNumber
- CB31054302
- Molecular Formula
- C8H15NO3
- Formula Weight
- 173.21
- MOL File
- 82353-56-8.mol
Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI) Property
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B814093
- Product name
- (R)-tert-Butyl(1-oxopropan-2-yl)carbamate
- Packaging
- 10mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 9055AH
- Product name
- (R)-Tert-butyl(1-oxopropan-2-yl)carbamate
- Packaging
- 100mg
- Price
- $167
- Updated
- 2021/12/16
- Product number
- 10R0328
- Product name
- (R)-(1-Methyl-2-oxo-ethyl)-carbamicacidtert-butylester
- Purity
- 96%
- Packaging
- 1g
- Price
- $188
- Updated
- 2021/12/16
- Product number
- A155075
- Product name
- (R)-tert-Butyl(1-oxopropan-2-yl)carbamate
- Purity
- 95%
- Packaging
- 1g
- Price
- $211
- Updated
- 2021/12/16
- Product number
- AA00G4C5
- Product name
- (R)-tert-Butyl(1-oxopropan-2-yl)carbamate
- Purity
- 97%
- Packaging
- 1g
- Price
- $356
- Updated
- 2021/12/16
Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI) Chemical Properties,Usage,Production
Synthesis
79069-13-9
82353-56-8
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