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HazMat fee for 500 gram (Estimated)
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USD 0.00
Limited Quantity
USD 15-60
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USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
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Structure of 4538-50-5 * Storage: {[proInfo.prStorage]}
* 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.
With water In neat (no solvent) at 23℃; Sealed tube
A 5 mL round-bottomed flask equipped with a stir bar and plastic cap was charged with oligomeric cyclic (R,R)-(salen)Co(III) triflate 4a (n=1–2) (3.1 mg, contained 9percent toluene by mass, 0.0035 mmol Co) and placed in a room temperature water bath. (±)-Methyl glycidate ((±)-S20) (1 mL, 11.4 mmol) was added followed immediately by H2O (122.5 μL, 6.80 mmol). The reaction was then stirred at room temperature. H2O had completely dissolved by 5 min; catalyst by 9 min. Aliquots were removed periodically, diluted with CH2Cl2, and filtered through a plug of silica to remove product diol. Ee was then determined by chiral GC analysis. Conversions were determined by taking a separate aliquot, diluting with CDCl3, and comparing starting epoxide and product diol 1H NMR integration values.
Reference:
[1] Tetrahedron, 2014, vol. 70, # 27-28, p. 4165 - 4180
[2] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
[3] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
2
[ 4538-50-5 ]
[ 18289-89-9 ]
[ 10303-88-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
[2] Journal of the American Chemical Society, 2004, vol. 126, # 5, p. 1360 - 1362
[3] Advanced Synthesis and Catalysis, 2006, vol. 348, # 18, p. 2619 - 2625
3
[ 4538-50-5 ]
[ 18289-89-9 ]
[ 10303-88-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
4
[ 4538-50-5 ]
[ 18289-89-9 ]
[ 4538-50-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
5
[ 67-56-1 ]
[ 201230-82-2 ]
[ 4538-50-5 ]
[ 617-55-0 ]
Reference:
[1] Journal of Organic Chemistry, 1999, vol. 64, # 7, p. 2164 - 2165
6
[ 4538-50-5 ]
[ 18289-89-9 ]
[ 10303-88-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
[2] Journal of the American Chemical Society, 2004, vol. 126, # 5, p. 1360 - 1362
[3] Advanced Synthesis and Catalysis, 2006, vol. 348, # 18, p. 2619 - 2625
7
[ 4538-50-5 ]
[ 10303-88-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
[2] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
8
[ 4538-50-5 ]
[ 18289-89-9 ]
[ 10303-88-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
9
[ 4538-50-5 ]
[ 10303-88-5 ]
[ 4538-50-5 ]
[ 4538-50-5 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1307 - 1315
10
[ 4538-50-5 ]
[ 198572-71-3 ]
[ 10303-88-5 ]
[ 1026546-72-4 ]
Reference:
[1] Angewandte Chemie - International Edition, 2004, vol. 43, # 30, p. 3952 - 3954
11
[ 4538-50-5 ]
[ 51877-54-4 ]
Reference:
[1] Journal of Organic Chemistry, 1992, vol. 57, # 3, p. 1029 - 1031
With water; In neat (no solvent); at 23℃;Sealed tube;
A 5 mL round-bottomed flask equipped with a stir bar and plastic cap was charged with oligomeric cyclic (R,R)-(salen)Co(III) triflate 4a (n=1-2) (3.1 mg, contained 9% toluene by mass, 0.0035 mmol Co) and placed in a room temperature water bath. (±)-Methyl glycidate ((±)-S20) (1 mL, 11.4 mmol) was added followed immediately by H2O (122.5 muL, 6.80 mmol). The reaction was then stirred at room temperature. H2O had completely dissolved by 5 min; catalyst by 9 min. Aliquots were removed periodically, diluted with CH2Cl2, and filtered through a plug of silica to remove product diol. Ee was then determined by chiral GC analysis. Conversions were determined by taking a separate aliquot, diluting with CDCl3, and comparing starting epoxide and product diol 1H NMR integration values.
With lithium trifluoromethanesulfonate; In acetonitrile; at 70℃; for 4.0h;
Step 4: Preparation of (5R)-2-hydroxy-3-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-propionic acid methyl ester 5-Amino-1-methyl-1,3-dihydro-indol-2-one (Step 3, 1.40 g, 8.63 mmol), methyl (2R)-glycidate (0.882 g, 8.63 mmol), and lithium trifluoromethanesulfonate (1.33 g, 8.63 mmol) in acetonitrile (15 ml) are heated at 70 C. for 4 hours. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by flash chromatography (70% EtOAc/Hexane) to give the title compound as a light brown solid. HPLC r.t. 2.44 min; MS for C13H16N2O4 m/z 265.0(M+H)+.
With lithium trifluoromethanesulfonate; In acetonitrile; at 50℃;
Step 3: Preparation of (R)-methyl 2-hydroxy-3-(l-methyl-lH-indazol-5-ylamino)propanoate (R)-Methyl oxirane-2-carboxylate (0.988 mL, 0.0113 mol), l-methyl-lH-indazol-5- amine (2.00 g, 0.0113 mol) and lithium trifluoromethanesulfonate (1.76 g, 0.0113 mol) in acetonitrile (25 mL) are heated at 50 0C overnight. The reaction solution is diluted with ethyl acetate, washed with water and brine, the organic layer dried (Mg2SO4) and evaporated. The residue is purified by flash chromatography (50% EtOAc/Hexanes) to give the title compound (0.870 g, 31%); HPLC (SYMMETRY C18 3.5 muM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 2.47 min; MS for C12H15N3O3 m/z 250.3(M+H)+.
In acetonitrile at 4℃; for 24h; enantioselective reaction;
Table 5, entry 5, (2R)-3-(2-bromo-benzyloxy)-2-hydroxy-propionic acid, methyl ester, (-)-S91
Followed procedure A. Employed 2-bromobenzyl alcohol (S90) (468 mg, 2.5 mmol), (±)-methyl glycidate ((±)-S20) (642 mg, 6.3 mmol), distilled CH3CN (0.36 mL), and a room temperature stock solution of oligomeric cyclic (R,R)-(salen)Co(III) triflate 4a (n=1-2) in CH3CN (0.0125 M, 200 μL, 0.0025 mmol). Worked up at 24 h with pyridinium p-toluenesulfonate(2 mg, 0.008 mmol). Purified by flash chromatography on silica gel (30%EtOAc/hexanes) to give 678 mg (94%) of a clear oil in >99% ee as determined by chiral HPLCanalysis [Chiracel OD, 5% EtOH/hexanes, 1 mL/min, 220 nm, tR (minor) = 17.4 min; tR (major)= 22.1 min].
With HO4S(1-)*K(1+)*13FH In 1,2-dichloro-ethane at 0 - 20℃;
4 Example 4: Synthesis of MFA precursor using Methyl Acrylate-Epoxide Route (KHSO4- 13HF, in DCE)
The first step, synthesis of methyl oxirane-2-carboxylate, was reported with 80% yield (B Ochiai and T Hirano, 2014). Methyl oxirane-2-carboxylate (102 mg, 1 mmol) was dissolved in 2 mL of DCE and cooled to 0 °C. KHSO4-13HF (435 mg, 1.1 mmol) was added to the solution dropwise while stirring. The reaction was stirred at room temperature overnight. Both starting material and epoxide opening product were observed. The GC retention time of epoxide opening product matched the retention time of desired product, methyl 2-fluoro-3-hydroxypropanoate. In addition, impurities at higher retention time were observed, which are possible products from epoxide polymerization.