| Identification | Back Directory | [Name]
NW-09-15-1 | [CAS]
81323-58-2 | [Synonyms]
-(s)
NW-09-15-1
BOC-HSE-OTBU
BOC-Hser-OtBU
N-Boc-L-hoMoserine Butyl Ester
N-Boc-L-homoserine tert-butyl ester
-tert-Butyl 2-((tert-butoxycarbonyl)
N-t-Butyloxycarbonyl-L-hoMoserine-t-butyl ester
tert-butyl (tert-butoxycarbonyl)-L-homoserinate
(2S)-tert-butyl 2-[N-Boc-amino]-4-hydroxybutanoate
N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester
(S)-tert-butyl 2-(tert-butoxycarbonylamino)-4-hydroxybutanoate
2(S)-2-tert-butoxycarbonylamino-4-hydroxybutyric acid tert-butyl ester
L-Homoserine, N-[(1,1-dimethylethoxy)carbonyl]-, 1,1-dimethylethyl ester
2-Methyl-2-propanyl N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-hoMoserinate | [Molecular Formula]
C13H25NO5 | [MDL Number]
MFCD08275190 | [MOL File]
81323-58-2.mol | [Molecular Weight]
275.34 |
| Chemical Properties | Back Directory | [Boiling point ]
393.4±37.0 °C(Predicted) | [density ]
1.071±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,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 Information | Back Directory | [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]
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 |
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