ChemicalBook--->CAS DataBase List--->155542-33-9

155542-33-9

155542-33-9 Structure

155542-33-9 Structure
IdentificationBack Directory
[Name]

D-Aspartic acid, N-[(1,1-diMethylethoxy)carbonyl]-, 4-(1,1-diMethylethyl) ester
[CAS]

155542-33-9
[Synonyms]

(Tert-Butoxy)Carbonyl D-Asp(OtBu)-OH
Boc-D-aspartic acid-β-tert-butyl ester
Boc-D-aspartic acid 4-tert-butyl ester
N-Boc-D-aspartic acid 4-tert-butyl ester
(R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)aMino)-4-oxobutanoic acid
(2R)-4-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid
D-Aspartic acid, N-[(1,1-diMethylethoxy)carbonyl]-, 4-(1,1-diMethylethyl) ester
[Molecular Formula]

C13H23NO6
[MDL Number]

MFCD01861313
[MOL File]

155542-33-9.mol
[Molecular Weight]

289.32
Chemical PropertiesBack Directory
[Boiling point ]

432.6±40.0 °C(Predicted)
[density ]

1.139±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[pka]

3.69±0.23(Predicted)
[Appearance]

White to yellow Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332-H315-H319-H335
[Precautionary statements ]

P280
[HS Code ]

2922498590
Spectrum DetailBack Directory
[Spectrum Detail]

D-Aspartic acid, N-[(1,1-diMethylethoxy)carbonyl]-, 4-(1,1-diMethylethyl) ester(155542-33-9)1HNMR
Hazard InformationBack Directory
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

D-Aspartic acid 4-tert-butyl ester

64960-75-4

D-Aspartic acid, N-[(1,1-diMethylethoxy)carbonyl]-, 4-(1,1-diMethylethyl) ester

155542-33-9

GENERAL METHOD: D-aspartic acid-4-tert-butyl ester (1.89 g, 10 mmol) was dissolved in a solvent mixture of tetrahydrofuran (20 mL) and water (12 mL) at 0 °C. After stirring for 5 minutes, di-tert-butyl dicarbonate (4.35 g, 20 mmol) was added slowly in portions, followed by sodium carbonate (4.20 g, 40 mmol). The reaction mixture was stirred at room temperature for 24 h. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was dissolved in 10% aqueous sodium bicarbonate solution (50 mL) and the aqueous phase was washed with ether (3 x 20 mL). After adjusting the pH of the aqueous phase to 4.0 with citric acid, the product was extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the target product Boc-O-tert-butyl-D-aspartic acid (4-tert-butoxy-2-(tert-butoxycarbonylamino)-4-oxobutanoic acid) as a colorless oil (2.82 g, 97% yield).

[References]

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4975 - 4978
[2] Patent: WO2017/24009, 2017, A1. Location in patent: Paragraph 0637
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