Structure of 88496-70-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 88496-70-2 |
Formula : | C5H9ClO3 |
M.W : | 152.58 |
SMILES Code : | O=C(OC)C[C@@H](O)CCl |
MDL No. : | MFCD00273367 |
InChI Key : | WMRINGSAVOPXTE-SCSAIBSYSA-N |
Pubchem ID : | 10920707 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H318-H412 |
Precautionary Statements: | P264-P270-P273-P280-P301+P312+P330-P305+P351+P338+P310-P501 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.4 g | With D-glucose In aq. phosphate buffer at 20℃; Green chemistry; Enzymatic reaction | 12.5 g of methyl 4-chloroacetoacetate and 125 mL of 0.1 M PBS buffer, 15.0 g of glucose were added.ThepH was adjusted to 6.7by stirring at room temperature,and 0.15 g of the main enzyme, 0.01 g of the coenzyme and 0.5 g of the dehydrogenase were added to the reaction system in one portion, and the reaction was completed.0.8 g of diatomaceous earth and 150 ml of toluene were added, stirred, and filtered.After the filtrate was washed with a 10percent by weight aqueous solution of sodium chloride, the organic layer was concentratedto give 10.4 g of a brownish yellow liquid, that is, methyl (R)-(+)-4-chloro-3-hydroxybutanoate.The active enzyme was not detected by the WOOD method. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With N-chloro-succinimide; triphenylphosphine In dichloromethane at 5 - 20℃; for 18.3333 h; | [00201] (R)-Methyl 4-chloro-3-hydroxybutanoate OH Q-o'To a solution of (R)-methyl 3,4-dihydroxybutanoate (125.1 g, 0.93 mol) in CH2Cl2 (1.8 L) was added PPh3 (244.5 g, 0.93 mol) and slowly added NCS (124.2g, 0.93 mol) under ice water cooling. The mixture was stirred at 5 0C for 20 min and then stirred for 18 h at room temperature. After evaporating the solvent, the residue was purified by column chromatography (P.E\\E.A 20:1-5:1, gradient) to give (R)-methyl 4-chloro-3-hydroxybutanoate (33 g, 26percent over 3 steps). 1H NMR (300MHz, CDCl3) ? 4.18-4.25 (m, 1 H), 3.68 (s, 3 H), 3.55-3.60 (m, 2 H), 3.32- 3.33 (d, J= 4.2 Hz, 1 H), 2.52-2.68 (m, 2 H). |
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