NW-09-15-1
- Product Name
- NW-09-15-1
- CAS No.
- 81323-58-2
- Chemical Name
- NW-09-15-1
- Synonyms
- tert-butyl (tert-butoxycarbonyl)-L-homoserinate;N-Boc-L-homoserine tert-butyl ester;-(s);NW-09-15-1;BOC-HSE-OTBU;BOC-Hser-OtBU;Boc-L-Homo-Serine Butyl Ester;N-Boc-L-hoMoserine Butyl Ester;-tert-Butyl 2-((tert-butoxycarbonyl);tert-Butyl (S)-2-(Boc-amino)-4-hydroxybutyrate
- CBNumber
- CB52487594
- Molecular Formula
- C13H25NO5
- Formula Weight
- 275.34
- MOL File
- 81323-58-2.mol
NW-09-15-1 Property
- Boiling point:
- 393.4±37.0 °C(Predicted)
- Density
- 1.071±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 10.91±0.46(Predicted)
- Appearance
- Colorless to light yellow Liquid
- InChI
- InChI=1S/C13H25NO5/c1-12(2,3)18-10(16)9(7-8-15)14-11(17)19-13(4,5)6/h9,15H,7-8H2,1-6H3,(H,14,17)/t9-/m0/s1
- InChIKey
- WFSWHDJTFHDJFE-VIFPVBQESA-N
- SMILES
- C(OC(C)(C)C)(=O)[C@H](CCO)NC(OC(C)(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
- B692910
- Product name
- N-(tert-Butoxycarbonyl)-(S)-homoserinetert-ButylEster
- Packaging
- 100mg
- Price
- $145
- Updated
- 2021/12/16
- Product number
- FB142033
- Product name
- (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate
- Packaging
- 50mg
- Price
- $160
- Updated
- 2021/12/16
- Product number
- AS87383
- Product name
- N-Boc-L-homoserine tert-butyl ester
- Purity
- 95+% ee
- Packaging
- 250mg
- Price
- $244
- Updated
- 2021/12/16
- Product number
- AAA0017709
- Product name
- (S)-TERT-BUTYL-2-(TERT-BUTOXYCARBONYLAMINO)-4-HYDROXYBUTANOATE
- Purity
- 95.00%
- Packaging
- 0.25G
- Price
- $250
- Updated
- 2021/12/16
- Product number
- FB142033
- Product name
- (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate
- Packaging
- 100mg
- Price
- $250
- Updated
- 2021/12/16
NW-09-15-1 Chemical Properties,Usage,Production
Uses
N-(tert-Butoxycarbonyl)-(S)-homoserine tert-Butyl Ester is used as a reactant in the synthesis of N-substituted sultam carboxylic acids as novel glycogen synthase activators.
Synthesis
34582-32-6
81323-58-2
General procedure for the synthesis of N-(tert-butoxycarbonyl)-(S)-homoserine tert-butyl ester from N-Boc-L-aspartic acid 1-tert-butyl ester: 1b) Boc-L-Asp-OtBu (3.00 g, 10.4 mmol) was dissolved in 1,2-dimethoxyethane (10 mL) at -15°C and 4-methylmorpholine (1.14 mL, 10.4 mmol) and isobutyl chloroformate (1.35 mL, 10.4 mmol) were added sequentially. The reaction mixture was stirred at -15°C for 10 min before the precipitate was removed by filtration and the precipitate was washed with cold 1,2-dimethoxyethane (20 mL). A solution of sodium borohydride (0.59 g, 15.6 mmol) in water (5 mL) was slowly added to the filtrate at -15°C. After 5 min, the reaction was terminated by adding water (250 mL). The reaction mixture was extracted with ethyl acetate, the organic layers were combined and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give tert-butyl N-(tert-butoxycarbonyl)-(S)-homoserine. Yield: 2.70 g, 9.81 mmol, 95% yield. MS (ESIpos): m/z = 276 [M+H]+. 1H-NMR (400 MHz, chloroform-d): δ[ppm] = 1.46 (s, 9H), 1.48 (s, 9H), 1.51-1.58 (m, 1H), 2.09-2.20 (m, 1H), 3.45 (br.s., 1H), 3.55-3.76 (m, 2H), 4.31-4.40 (m, 1H). 5.35 (d, 1H).
References
[1] Patent: EP2322500, 2011, A1. Location in patent: Page/Page column 26-27
[2] Patent: WO2011/57986, 2011, A1. Location in patent: Page/Page column 53
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6656 - 6667
[4] Organic Letters, 2001, vol. 3, # 20, p. 3153 - 3155
[5] Tetrahedron, 2017, vol. 73, # 9, p. 1265 - 1274
NW-09-15-1 Preparation Products And Raw materials
Raw materials
Preparation Products
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