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CAS No. : | 27848-80-2 | MDL No. : | MFCD00065512 |
Formula : | C3H5LiO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GKQWYZBANWAFMQ-DKWTVANSSA-M |
M.W : | 96.01 | Pubchem ID : | 23687877 |
Synonyms : |
(S)-2-Hydroxypropanoic acid lithium
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 17.53 |
TPSA : | 60.36 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.4 cm/s |
Log Po/w (iLOGP) : | -12.79 |
Log Po/w (XLOGP3) : | -0.72 |
Log Po/w (WLOGP) : | -1.88 |
Log Po/w (MLOGP) : | -0.85 |
Log Po/w (SILICOS-IT) : | -0.8 |
Consensus Log Po/w : | -3.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.08 |
Solubility : | 117.0 mg/ml ; 1.21 mol/l |
Class : | Highly soluble |
Log S (Ali) : | -0.07 |
Solubility : | 81.4 mg/ml ; 0.848 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.98 |
Solubility : | 923.0 mg/ml ; 9.62 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
With cesium iodide; In N,N-dimethyl-formamide; at 20℃; | <strong>[27848-80-2]L-lactic acid lithium salt</strong> (18 mg) and cesium iodide (14 mg) was suspended in DMF (1 ml) and solution of chloromethyl (45,,5 -5-((2,S,)-2- [(3-amino-2,2-dimethyl-3- oxopropyl)amino]carbonyl}-3-methylbutyl)-4- {(25)-2-[4-methoxy-3-(3- methoxypropoxy)benzyl]-3-methylbutyl} - l ,3-oxazolidine-3-carboxylate (30 mg) in DMF (1 ml) was added and stirred at r.t. overnight. Reaction mixture was mixed with 10% citric acid (30 ml) and extracted into EtOAc (4x20 ml). Organic extracts were washed with brine and dried over MgS04. Concentrated by rotary evaporation and purified by column chromatography on silica gel (EtOAc/THF 9: 1 ) to give 19 mg of colorless oil. LCMS: 710.5 [M+l ]+, 732.5 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In tetrahydrofuran; at 0 - 20℃; for 3.0h; | Lac-OCA was prepared as described previously [9-11], however, triphosgene was used rather than diphosgene. Briefly, the lithium salt of L-lactic acid (0.5 mol) was suspended in anhydrous THF (350 mL) at 0 C. Next, a solution containing triphosgene (0.3 mol) in anhydrous THF (150 mL) was added dropwise at 0-5 C, and the reaction mixture was stirred at room temperature for 3 h. THF was removed under reduced pressure, and diethyl ether (1 L) was added to the residue. Lastly, the lithium salts were removed by filtration, and recrystallization from tert-butyl methyl ether afforded colorless crystals in 59% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere; | (S)-2-((tert-butyldimethylsilyl)oxy)propanoyl chloride was prepared based on the modification of the reported procedure (Organic Letters, 16(9), 2322-2325; 2014). To a solution of <strong>[27848-80-2]lithium (S)-2-hydroxypropanoate</strong> (2.88 g, 30 mmol) in DMF (30 mL) at 0 C under N2 was added TBSC1 (9 g, 60 mmol) and imidazole (8.2 g, 120 mmol). The reaction mixture was allowed to warm to r.t. and stirred overnight. The reaction mixture was partitioned between hexanes (300 mL) and saturated NaHC03 solution (300 niL). The organic layer was separated, washed with brine (30mL X 5). The organic layer was dried and concentrated to provide a crude oil (9.2g). The crude was dissolved in DCM (60 niL) and the solution was cooled to 0 C under N2. DMF (0.43 mL) was added followed by the dropwise addition of a solution of oxalyl chloride (1.3 eq, 39 mmol, 3.3 mL) in DCM (10 mL). The reaction mixture was allowed to warm to r.t. and stirred for another. All the volatiles were removed under vacuum and the residue was dissolved in DCM ( 10 mL). This solution was added to a solution of HYC-162 ( 1.92 g, 10 mmol) in DCM (90 mL) and DIPEA (7 ml,, 40 mmol) at 0 C under N2 . The reaction mixture was allowed to warm to r.t. and stirred for 1 h prior to being quenched with saturated NaHC03 and extracted with DCM (3x50 mL). The combined organic layer was washed with water and then, dried (Na2S04), filtered and then concentrated The oil was chromatographed on silica gel (1: 16 to 1:8 ethyl acetate /hexanes) to give title compound as an oil: (3.1 g, 82%.). 1H NMR (400 MHz, CDC13) delta 11.99 (s, 1H), 6.68 (s, 1H), 4.47 (q, J= 6.7 Hz, 1H), 3.94 (s, 3H), 1.51 (d, J = 6.7, 3H), 1.00 (s, 9H), 0.20 (s, 6H). |