Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate
- Product Name
- Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate
- CAS No.
- 184429-84-3
- Chemical Name
- Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate
- Synonyms
- 1-(Boc-amino)-3-(TBDMS-oxy)-2-propanone;3-(Bc-Amino)-1-[(Tert-Butyldimethylsilyl)Oxy]-2-Propanone;3-(Boc-amino)-1-[(tert-butyldimethylsilyl)oxy]-2-propanone;tert-Butyl (3-((tert-butyldimethylsilyl)oxy)-2-oxopropyl)carbamate;Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate;Carbamic acid, N-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-oxopropyl]-, 1,1-dimethylethyl ester
- CBNumber
- CB13144586
- Molecular Formula
- C14H29NO4Si
- Formula Weight
- 303.47
- MOL File
- 184429-84-3.mol
Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate Property
- Boiling point:
- 347.5±27.0 °C(Predicted)
- Density
- 0.975±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 10.85±0.46(Predicted)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
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
- 4326AQ
- Product name
- tert-butylN-[3-[tert-butyl(dimethyl)silyl]oxy-2-oxopropyl]carbamate
- Packaging
- 1g
- Price
- $462.8
- Updated
- 2021/12/16
- Product number
- 4326AQ
- Product name
- tert-butylN-[3-[tert-butyl(dimethyl)silyl]oxy-2-oxopropyl]carbamate
- Packaging
- 250mg
- Price
- $255.2
- Updated
- 2021/12/16
- Product number
- A225769
- Product name
- tert-Butyl(3-((tert-butyldimethylsilyl)oxy)-2-oxopropyl)carbamate
- Purity
- 95+%
- Packaging
- 1g
- Price
- $274
- Updated
- 2021/12/16
- Product number
- DA-1408
- Product name
- 1-(Boc-amino)-3-(TBDMS-oxy)-2-propanone
- Purity
- 97%
- Packaging
- 5g
- Price
- $339.17
- Updated
- 2021/12/16
- Product number
- SY124739
- Product name
- 3-(Boc-amino)-1-[(tert-butyldimethylsilyl)oxy]-2-propanone
- Purity
- ≥95%
- Packaging
- 10g
- Price
- $475
- Updated
- 2021/12/16
Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate Chemical Properties,Usage,Production
Synthesis
195197-94-5
184429-84-3
Oxalyl chloride (13.6 mL, 0.16 mol) was dissolved in anhydrous dichloromethane (150 mL) under nitrogen protection and cooled to -78 °C. Dimethyl sulfoxide (15.2 mL, 0.21 mol) was slowly added dropwise over 30 min, and after completion of the dropwise addition, stirring was continued for 1 h at -78 °C. Subsequently, a solution of tert-butyl 3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropylcarbamate (32.6 g, 0.11 mol) in dichloromethane (50 mL) was added dropwise over 20 minutes. After the reaction mixture continued to be stirred at -78 °C for 1 h, triethylamine (59.6 mL, 0.43 mol) was added. The cooling bath was removed and the reaction mixture was allowed to slowly warm to room temperature. The reaction mixture was transferred to a partitioning funnel, water (100 mL) and dichloromethane (70 mL) were added for partitioning, and the aqueous layer was further extracted with dichloromethane (2 x 70 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under nitrogen protection. The crude product was purified by silica gel column chromatography using 5% ethyl acetate in hexane solution as eluent to afford tert-butyl 3-((tert-butyldimethylsilyl)oxy)-2-oxopropylcarbamate (29.8 g, 92%) as a light yellow oil.1H-NMR (300 MHz, CDCl3) δ: 0.11 (6H, s), 0.94 (9H, s), and 1.47 (9H, s), 3.92 (2H, s), 4.26 (2H, d, J=4.6 Hz), 5.22 (1H, br s).
References
[1] Patent: WO2013/163675, 2013, A1. Location in patent: Paragraph 00182
[2] Canadian Journal of Chemistry, 1997, vol. 75, # 7, p. 942 - 948
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1191 - 1197
[4] Journal of Pharmacology and Experimental Therapeutics, 2013, vol. 347, # 2, p. 365 - 374
Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate Preparation Products And Raw materials
Raw materials
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