Z-ASP(OME)-OH
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Z-ASP(OME)-OH
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CAS No:
3160-47-2
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Formula:
C13H15NO6
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Chemical Name:
Z-ASP(OME)-OH
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Synonyms:
Z-ASP(OME)-OH;CBZ-ASP(OME)-OH;Z-ASPARTICACID(OME)-OH;Z-L-ASPARTICACIDB-METHYLESTER;Z-L-ASPARTICACID4-METHYLESTER;CBZ-L-ASPARTICACID4-METHYLESTER;Z-L-ASPARTICACIDBETA-METHYLESTER;N-cbz-L-asparticacidB-methylester;CBZ-L-ASPARTICACIDBETAMETHYLESTER;N-CBZ-L-ASPARTICACIDBETA-METHYLESTER
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CAS No:
Z-ASP(OME)-OH Use and Manufacturing
30.5 g (207 mmol) of (S)-2-amino-4-methoxy-4-oxobutanoic acid obtained in Step 1-2(1) was dissolved in 726 mL of distilled water, and 260 mL of diethyl ether was added thereto. 40.15 g (290 mmol) of potassium carbonate was added and dissolved, and then 41.5 mL (290 mmol) of benzyl chloroformate was added thereto. The mixture was stirred at room temperature for 4 hours. After phase-separation, the organic layer was discarded. The aqueous layer was washed with diethyl ether several times, and was adjusted to pH 1 with 1 N hydrochloric acid. The aqueous layer was extracted with diethyl ether several times, dried over magnesium sulfate, and concentrated under vacuum to give 55 g of the title compound (yield: 94percent). This is a known compound. Goodman, Murray; Boardman, Franklin; J. Amer. Chem. Soc. 1963, 85, 2483-90. The crude compound 4-9 (9.8 g, 53 mmol) was dissolved in water (115 mL) and dioxane (53 mL), and cooled to 0 °C. Na2CO3 (5.6 g, 53 mmol) was added, followed by benzyl chloroformate (9.1 g, 53.4 mmol) in dioxane (63 mL) dropwise over 3 h. The reaction mixturewas stirred at ambient temperature overnight. The solution was washed with ethyl acetate (3 x 50 mL). The aqueous layer was acidified to pH 2 with 6 M HC1. The product was extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2 SO4 and the solvent was evaporated under reduced pressure. The crude compound was passed through a short pad of silica gel using ethyl acetate and concentrated to providecompound 4-10 as a semi-solid (78percent).L-Aspartic acid (10.0 g, 75.1 mmol) was added to MeOH (50 mL) and cooled to -30 °C. SOCl
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