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[ CAS No. 39637-99-5 ] {[proInfo.proName]}

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Chemical Structure| 39637-99-5
Chemical Structure| 39637-99-5
Structure of 39637-99-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 39637-99-5 ]

CAS No. :39637-99-5 MDL No. :MFCD00044400
Formula : C10H8ClF3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PAORVUMOXXAMPL-VIFPVBQESA-N
M.W : 252.61 Pubchem ID :3080792
Synonyms :

Safety of [ 39637-99-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 39637-99-5 ]

* 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.

  • Downstream synthetic route of [ 39637-99-5 ]

[ 39637-99-5 ] Synthesis Path-Downstream   1~66

  • 1
  • [ 73349-08-3 ]
  • [ 39637-99-5 ]
  • [ 73349-12-9 ]
  • 2
  • [ 39637-99-5 ]
  • [ 73349-07-2 ]
  • [ 73349-11-8 ]
  • 3
  • [ 124602-03-5 ]
  • [ 39637-99-5 ]
  • [ 124575-34-4 ]
  • [ 124575-35-5 ]
YieldReaction ConditionsOperation in experiment
In pyridine; tetrachloromethane for 16h;
  • 4
  • [ 2041-14-7 ]
  • [ 39637-99-5 ]
  • [ 115463-93-9 ]
  • 5
  • [ 24621-61-2 ]
  • [ 39637-99-5 ]
  • bis-(R)-MTPA ester of (S)-(+)-1,3-butanediol [ No CAS ]
  • 6
  • [ 6290-03-5 ]
  • [ 39637-99-5 ]
  • bis-(R)-MTPA ester of (R)-(-)-1,3-butanediol [ No CAS ]
  • 7
  • [ 53562-86-0 ]
  • [ 39637-99-5 ]
  • [ 76904-97-7 ]
YieldReaction ConditionsOperation in experiment
20 mg With pyridine In tetrachloromethane Ambient temperature;
  • 9
  • [ 52780-14-0 ]
  • [ 39637-99-5 ]
  • 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-(3-bromo-phenyl)-ethyl ester [ No CAS ]
  • 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 1-(3-bromo-phenyl)-ethyl ester [ No CAS ]
  • 11
  • [ 13674-16-3 ]
  • [ 39637-99-5 ]
  • [ 76905-04-9 ]
  • 12
  • [ 454-91-1 ]
  • [ 39637-99-5 ]
  • 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-(3-trifluoromethyl-phenyl)-ethyl ester [ No CAS ]
  • 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-(3-trifluoromethyl-phenyl)-ethyl ester [ No CAS ]
  • 13
  • [ 10482-56-1 ]
  • [ 39637-99-5 ]
  • (S,S)-α-methoxy-α-(((trifluoromethyl)phenyl)acetyl) ester (R)-terpineol [ No CAS ]
  • 14
  • [ 149055-86-7 ]
  • [ 39637-99-5 ]
  • (1S,3R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-cyclohexanecarboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With pyridine; dmap In dichloromethane Ambient temperature;
  • 15
  • [ 37722-82-0 ]
  • [ 39637-99-5 ]
  • (1S,3R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-cyclohexanecarboxylic acid methyl ester [ No CAS ]
  • (1S,3S)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-cyclohexanecarboxylic acid methyl ester [ No CAS ]
  • (1R,3R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-cyclohexanecarboxylic acid methyl ester [ No CAS ]
  • (1R,3S)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-cyclohexanecarboxylic acid methyl ester [ No CAS ]
  • 16
  • [ 943-73-7 ]
  • [ 39637-99-5 ]
  • (S)-4-Phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-butyric acid [ No CAS ]
  • 17
  • [ 62624-46-8 ]
  • [ 39637-99-5 ]
  • [ 123724-34-5 ]
YieldReaction ConditionsOperation in experiment
In pyridine; tetrachloromethane
  • 18
  • [ 61586-46-7 ]
  • [ 39637-99-5 ]
  • [ 123724-34-5 ]
YieldReaction ConditionsOperation in experiment
In pyridine; tetrachloromethane
  • 19
  • [ 39637-99-5 ]
  • [ 137496-71-0 ]
  • (R)-3,3,3-Trifluoro-2-methoxy-1-((S)-2-methyl-pyrrolidin-1-yl)-2-phenyl-propan-1-one [ No CAS ]
  • 20
  • [ 39637-99-5 ]
  • [ 87860-35-3 ]
  • (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-phenoxy-propyl ester [ No CAS ]
  • 21
  • [ 39637-99-5 ]
  • [ 112018-26-5 ]
  • [ 111934-09-9 ]
  • 22
  • [ 39637-99-5 ]
  • [ 77087-60-6 ]
  • [ 126046-29-5 ]
  • 23
  • [ 39637-99-5 ]
  • [ 63060-94-6 ]
  • [ 121269-59-8 ]
  • 24
  • [ 39637-99-5 ]
  • [ 73913-65-2 ]
  • [ 121269-60-1 ]
YieldReaction ConditionsOperation in experiment
52% With triethylamine In chloroform at 0℃;
  • 25
  • [ 39637-99-5 ]
  • [ 175-96-2 ]
  • 2,7-Bis(α-methoxy-α-(fluoromethyl)phenylacetyl)-2,7-diazaspiro<4.4>nonane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In tetrachloromethane overnight;
  • 26
  • [ 2914-69-4 ]
  • [ 39637-99-5 ]
  • [ 133796-97-1 ]
  • 27
  • [ 53562-86-0 ]
  • [ 39637-99-5 ]
  • methyl (3S)-3-<(S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl>butyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With pyridine In tetrachloromethane for 12h; Ambient temperature;
  • 28
  • [ 39637-99-5 ]
  • [ 3976-69-0 ]
  • methyl (3R)-3-<(S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl>butyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With pyridine In tetrachloromethane for 12h; Ambient temperature;
  • 29
  • [ 39637-99-5 ]
  • [ 6091-44-7 ]
  • (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-1-piperidin-1-yl-propan-1-one [ No CAS ]
  • 30
  • [ 110-86-1 ]
  • [ 39637-99-5 ]
  • [ 63738-92-1 ]
  • (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-methyl-2-sulfo-ethyl ester; compound with pyridine [ No CAS ]
  • (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methyl-2-sulfo-ethyl ester; compound with pyridine [ No CAS ]
  • 31
  • [ 39637-99-5 ]
  • [ 267401-33-2 ]
  • C21H19F4NO5 [ No CAS ]
  • 32
  • [ 39637-99-5 ]
  • [ 5746-86-1 ]
  • (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-1-(2-pyridin-3-yl-pyrrolidin-1-yl)-propan-1-one [ No CAS ]
  • 33
  • [ 39637-99-5 ]
  • [ 494-97-3 ]
  • (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-1-((S)-2-pyridin-3-yl-pyrrolidin-1-yl)-propan-1-one [ No CAS ]
  • 34
  • [ 42969-65-3 ]
  • [ 39637-99-5 ]
  • [ 160156-04-7 ]
  • 35
  • [ 42890-76-6 ]
  • [ 39637-99-5 ]
  • (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-propyl ester [ No CAS ]
  • 36
  • [ 39637-99-5 ]
  • [ 296774-32-8 ]
  • (2S,3S)-3-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; potassium carbonate In 1,4-dioxane at 20℃; for 0.25h;
  • 37
  • [ 56523-47-8 ]
  • [ 39637-99-5 ]
  • (2S)-2-phenylpyrrolidine-(S)-MTPA-amide [ No CAS ]
  • 38
  • [ 3219-63-4 ]
  • [ 39637-99-5 ]
  • (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid trimethylsilanylmethyl ester [ No CAS ]
  • 39
  • [ 37617-33-7 ]
  • [ 39637-99-5 ]
  • (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-2,2-dimethyl-cyclopentyl ester [ No CAS ]
  • (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2,2-dimethyl-cyclopentyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine
  • 40
  • [ 2549-14-6 ]
  • [ 39637-99-5 ]
  • 3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid 1-phenyl-2-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-ethyl ester [ No CAS ]
  • 41
  • [ 39637-99-5 ]
  • [ 7076-23-5 ]
  • C19H19F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
  • 42
  • [ 39637-99-5 ]
  • [ 1006-64-0 ]
  • C20H20F3NO2 [ No CAS ]
  • 43
  • [ 26549-24-6 ]
  • [ 39637-99-5 ]
  • (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (R)-2-hexyl ester [ No CAS ]
  • 44
  • [ 6033-24-5 ]
  • [ 39637-99-5 ]
  • (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (R)-2-heptyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With pyridine In dichloromethane
  • 45
  • [ 80866-87-1 ]
  • [ 39637-99-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrolysis 2: 10.5 g / SOCl2
  • 46
  • [ 587-33-7 ]
  • [ 39637-99-5 ]
  • [ 960622-69-9 ]
YieldReaction ConditionsOperation in experiment
sodium hydrogencarbonate; In water; acetone; at 0 - 20℃; for 1h; Reference samples of the (S)- and (i?)-2-methoxy-2- trifluoromethyl-2-phenylacetic acid ((S)- and (i?)-MTPA) derivatives of L-V- hydroxyphenylalanine were prepared as follows. To a well-stirred solution of 0.5 mg of L-3' -hydroxyphenylalanine in 0.5 ml of water at 0 C were added 0.5 ml of aqueous NaHCO3-solution, 1 ml of acetone, and 4 mul of either (R)- or (S)-2- methoxy-2-trifluoromethyl-2-phenylacetic acid chloride ((R)- and (/S)-MTPA-Cl). The resulting mixture was stirred for 1 h at 20 C. Subsequently, the acetone was evaporated in vacuo using a rotary evaporator, and the aqueous residue was extracted with 1 ml of ether. The organic extract was filtered over a pad of anhydrous Na2SO4 and evaporated to dryness in vacuo. The residue was dissolved in 0.6 ml of acetone-d6 and the resulting solution analyzed by 1H-NMR spectroscopy. The diastereomeric (S)- and (i?)-MTPA derivatives of L-V- hydroxyphenylalanine showed significant differences in their 1H-NMR spectra. Characteristic signals include protons 3-Halphaand 3 -Hp ((R)-MTPA derivative [from (S)-MTP A-Cl] delta 3.09 ppm and 3.24 ppm; (S)-MTPA derivative [from (^)-MTPA- Cl] delta 3.02 ppm and 3.19 ppm).
  • 47
  • [ 26214-65-3 ]
  • [ 7031-27-8 ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-hydroxymethyl-2-oxazolidinone [ No CAS ]
  • [ 38870-89-2 ]
  • [ 2251-50-5 ]
  • [ 39637-99-5 ]
  • [ 10313-60-7 ]
  • [ 4023-34-1 ]
  • [ 53064-54-3 ]
  • [ 5538-51-2 ]
  • [ 157373-08-5 ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2-methoxyacetyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(cyclopropanecarbonyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(furan-3-carbonyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(isoxazole-3-carbonyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2-(phenylthio)acetyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(3,4-dimethoxybenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2-acetoxybenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(2,3,4-trifluorobenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
  • (S)-3-(2,5-dimethoxyphenacyl)-5-(perfluorobenzoyloxy)methyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine; dichloromethane at 20℃; Combinatorial reaction / High throughput screening (HTS); 3 To about 295 mg (1.0 mmoles) of (S)-3- (2,5-dimethocyphenacyl) -5- hydroxymethyl-2-oxazolidinone in dry CH2Cl2 (8 mL CH2Cl2), 1.0 equiv. (1.1 mmoles) of pyridine was added and the reaction mixture stirred at room temperature. To this reaction mixture was added 1.0 equiv. of a mixture of ten different acetyl chlorides. The reaction was stirred overnight at room temperature. Afterwards, TLC of an aliquot indicated that complete conversion of the (S)-3- (2,5-dimethocyphenacyl) -5- hydroxymethyl-2-oxazolidinone to (S)-3- (2,5- dimethocyphenacyl)-5- (substituted methyl) -2- oxazolidinone had occurred. Therefore, about 3 mL of 20% NH4Cl was added to the reaction mixture and the organic layer removed and saved. The aqueous layer was extracted two times with 40 mL aliquots of CH2Cl2. The CH2Cl2 extracts were combined with the saved organic layer and the mixture dried with 2.5 g anhydrous Na2SO4. The mixture was then concentrated in vacuo to provide a crude product. The crude product was analyzed by 1H-NMR, 13C NMR, HPLC, and TLC using a EtOAc: hexane (2: 1) solvent system. An HPLC profile of the (S)-3- (2,5- dimethocyphenacyl)-5- (substituted methyl) -2- oxazolidinone products made is shown in Figure 3. The products represented by the peaks in the HPLC are shown in Figure 4. This example illustrates the principle of the present invention. As shown by this example, providing n=10 acetyl halides in a single reaction produces 10 (S)-3- (2,5-dimethocyphenacyl) -5- (substituted methyl) -2-oxazolidinone products. If n=10 aryl bromides had been used as well to arylate the N at the 3-position, the process would have generated 100 (S)-3- (substituted)-5- (substituted methyl) -2-oxazolidinone products.
  • 48
  • [ 1000210-48-9 ]
  • [ 39637-99-5 ]
  • [ 1779-49-3 ]
  • C16H20F3NO2 [ No CAS ]
  • C16H20F3NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (R)-3-aminopentan-2-one; Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With acetyl chloride In methanol at 20℃; for 1h; Stage #3: (R)-methoxytrifluoromethylphenylacetyl chloride With triethylamine In dichloromethane at 20℃; for 2h; Further stages. Title compound not separated from byproducts.;
  • 49
  • [ 39637-99-5 ]
  • [ 928-68-7 ]
  • C18H25F3O3 [ No CAS ]
  • C18H25F3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-methylheptan-2-one With dichloro(benzene)ruthenium(II) dimer; mono(3-deoxy-3-[N-(2-hydroxyethyl)amino])-β-cyclodextrin; sodium formate In water; N,N-dimethyl-formamide at 50℃; for 12h; Stage #2: (R)-methoxytrifluoromethylphenylacetyl chloride With pyridine for 0.5h; optical yield given as %ee; enantioselective reaction;
  • 50
  • [ 56523-47-8 ]
  • [ 39637-99-5 ]
  • (2R)-2-phenylpyrrolidine-(S)-MTPA-amide [ No CAS ]
  • 51
  • [ 13524-04-4 ]
  • [ 39637-99-5 ]
  • [ 131864-75-0 ]
  • 52
  • [ 770-35-4 ]
  • [ 39637-99-5 ]
  • C19H19F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap In dichloromethane at 20℃; for 16h; 3.13. General procedure for preparation of the MTPA esters General procedure: To a stirred solution of the alcohol (15 mg), pyridine (0.1 mL), and 4,4-dimethylaminopyridine (1-2 crystals) in CH2Cl2 (0.5 mL) was injected (R)-MTPA chloride (25 mg) in CH2Cl2 (0.5 mL). After stirring the mixture for 16 h at room temperature, the excess pyridine was removed by purging with N2 gas, and the residue subjected to preparative thin-layer chromatography (silica gel, 10% EtOAc/hexane) to isolate the respective MTPA esters. The 1H NMR analyses were carried out with the pure samples. The MTPA esters of the racemic alcohols were also prepared as above and the diagnostic 1H NMR methoxyl resonances for them were as follows: 3b. 1H NMR: δ 3.37 and 3.50; 5b. 1H NMR: δ 3.40 and 3.49; 6b. 1H NMR: δ 3.40 and 3.48; 8b. 1H NMR: δ 3.40 and 3.49; 10b. 1H NMR: δ 3.39 and 3.48; 11b. 1H NMR: δ 3.46 and 3.59; 12b. 1H NMR: δ 3.45 and 3.59; 13b. 1H NMR: δ 3.46 and 3.56; 14b. 1H NMR: δ 3.45 and 3.55.
  • 53
  • [ 613-87-6 ]
  • [ 39637-99-5 ]
  • (S)-1-phenylpropyl (S)-α-methoxy-α-trifluoromethylphenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap; In dichloromethane; at 20℃; for 16h; General procedure: To a stirred solution of the alcohol (15 mg), pyridine (0.1 mL), and 4,4-dimethylaminopyridine (1-2 crystals) in CH2Cl2 (0.5 mL) was injected (R)-MTPA chloride (25 mg) in CH2Cl2 (0.5 mL). After stirring the mixture for 16 h at room temperature, the excess pyridine was removed by purging with N2 gas, and the residue subjected to preparative thin-layer chromatography (silica gel, 10% EtOAc/hexane) to isolate the respective MTPA esters. The 1H NMR analyses were carried out with the pure samples. The MTPA esters of the racemic alcohols were also prepared as above and the diagnostic 1H NMR methoxyl resonances for them were as follows: 3b. 1H NMR: δ 3.37 and 3.50; 5b. 1H NMR: δ 3.40 and 3.49; 6b. 1H NMR: δ 3.40 and 3.48; 8b. 1H NMR: δ 3.40 and 3.49; 10b. 1H NMR: δ 3.39 and 3.48; 11b. 1H NMR: δ 3.46 and 3.59; 12b. 1H NMR: δ 3.45 and 3.59; 13b. 1H NMR: δ 3.46 and 3.56; 14b. 1H NMR: δ 3.45 and 3.55.
  • 54
  • [ 19578-92-8 ]
  • [ 39637-99-5 ]
  • C21H23F3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap In dichloromethane at 20℃; for 16h; 3.13. General procedure for preparation of the MTPA esters General procedure: To a stirred solution of the alcohol (15 mg), pyridine (0.1 mL), and 4,4-dimethylaminopyridine (1-2 crystals) in CH2Cl2 (0.5 mL) was injected (R)-MTPA chloride (25 mg) in CH2Cl2 (0.5 mL). After stirring the mixture for 16 h at room temperature, the excess pyridine was removed by purging with N2 gas, and the residue subjected to preparative thin-layer chromatography (silica gel, 10% EtOAc/hexane) to isolate the respective MTPA esters. The 1H NMR analyses were carried out with the pure samples. The MTPA esters of the racemic alcohols were also prepared as above and the diagnostic 1H NMR methoxyl resonances for them were as follows: 3b. 1H NMR: δ 3.37 and 3.50; 5b. 1H NMR: δ 3.40 and 3.49; 6b. 1H NMR: δ 3.40 and 3.48; 8b. 1H NMR: δ 3.40 and 3.49; 10b. 1H NMR: δ 3.39 and 3.48; 11b. 1H NMR: δ 3.46 and 3.59; 12b. 1H NMR: δ 3.45 and 3.59; 13b. 1H NMR: δ 3.46 and 3.56; 14b. 1H NMR: δ 3.45 and 3.55.
  • 56
  • [ 56618-58-7 ]
  • [ 39637-99-5 ]
  • methyl (R)-3-(((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl)oxy)decanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With pyridine at 20℃; for 3h; Inert atmosphere;
With pyridine In tetrachloromethane at 20℃; for 12h;
  • 57
  • [ 39637-99-5 ]
  • [ 19525-87-2 ]
  • C21H22F3NO5 [ No CAS ]
  • 59
  • [ 2425-28-7 ]
  • [ 39637-99-5 ]
  • C18H16BrF3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With pyridine In dichloromethane at 20℃;
  • 60
  • [ 1174020-44-0 ]
  • [ 39637-99-5 ]
  • [ 1418193-08-4 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine In dichloromethane at 20℃; for 22h; Cooling with ice; Preparation of tert-butyl (3 S,4S)-3-fluoro-4-[(2 S)-3, 3,3-trifluoro-2-methoxy-2- henylroanoyl1oxy)jjierid me-i -carboxylate Preparation of te/t-butyl (3S,4SV3-fluoro-4-fr(2S)-3,3,3-trifluoro-2-methoxy-2- phenylpropanoylloxy}piperidine-1 -carboxylateTo a stirred, cold (degrees Celsius) solution of the tert-butyl (3S,4S)-3-fluoro-4- hydroxypiperidine-1-carboxylate (Enantiomer 2 from above) (20 mg, 0.09 mmol) and pyridine (22 μΙ_, 0.27 mmol) in dichloromethane (0.3 mL) was added (2f?)-3,3,3-trifluoro- 2-methoxy-2-phenylpropanoyl chloride (34 μΙ_, 0.18 mmol) via microsyringe. The ice bath was then removed and the suspension was stirred for 22 hours at roomtemperature. The mixture was diluted with dichloromethane and aqueous sodium bicarbonate solution before it was extracted with dichloromethane (3 x 10 mL). The combined organic extracts were dried over sodium sulfate, filtered and the filtrate was concentrated under vacuum. The clear residue was pre-adsorbed onto 5 g of silica and purified by chromatography on 4 g silica, eluting with a gradient mixture of 0-20% ethyl acetate in heptane to give the title compound as a clear, colorless, viscous oil (41 mg, 100%). 1 H NMR (500 MHz, deuterochloroform) delta ppm 1.45 (s, 9 H) 1 .52 - 1.64 (m, 1 H) 2.06 - 2.13 (m, 1 H) 3.04 - 3.16 (m, 1 H) 3.22 (br. s., 1 H) 3.58 (d, J=0.98 Hz, 3 H) 3.70 - 3.81 (m, 1 H) 3.91 - 4.28 (m, 1 H) 4.39 - 4.61 (m, 1 H) 5.18 - 5.28 (m, 1 H) 7.38 - 7.46 (m, 3 H) 7.49 - 7.56 (m, 2 H). TLC: Rf: 0.27 in 15% ethyl acetate/heptane
  • 61
  • [ 24915-95-5 ]
  • [ 39637-99-5 ]
  • C16H19F3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; enantioselective reaction;
  • 62
  • [ 823-19-8 ]
  • [ 39637-99-5 ]
  • C16H17F3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; enantioselective reaction;
  • 63
  • [ 1561-86-0 ]
  • [ 39637-99-5 ]
  • C16H18ClF3O3 [ No CAS ]
  • C16H18ClF3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 20℃; for 15h; Inert atmosphere;
  • 64
  • [ 13171-64-7 ]
  • [ 39637-99-5 ]
  • C26H24F6O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; General procedure: Compounds 1-6 and 10-11 (3.0 mg each) were, respectively, dissolved in 100 muL methanol and added to 100 muL 10% K2CO3 (methanol/water 2: 1, v/v). After hydrolysis at 60C for 2 h, the reaction mixtures were blow-dried, then acidified by 0.1 M HCl (500 muL) and extracted with EtOAc (500 muL×3). The aqueous layers were blow-dried and dissolved in methanol (200 muL). A drop of SOCl2 was added to the solution to catalyze the esterification (room temperature, 12 h). After evaporation, the mixed methyl esters of 4-hydroxytiglic acid and malic acid (or tartaric acid) were dissolved in dry pyridine (100 muL) and reacted with (S)-MTPA chloride (2 muL) overnight to obtain the final products. The corresponding authentic (R)-MTPA esters were also prepared from the commercial D-malic acid, L-malic acid, D-tartaric acid and L-tartaric acid. The 1H NMR data of the authentic (R)-MTPA esters of dimethyl malates were in accord with the reported.8
  • 65
  • [ 39637-99-5 ]
  • [ 82578-45-8 ]
  • C18H23F3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; dmap; In dichloromethane; at 20℃; for 16.0h; General procedure: A mixture of (R)-MTPA (25mg) and SOCl2 (0.250ml) in toluene (2ml) was refluxed for 3h. After removing the excess SOCl2 in vacuum, the resultant MTPA chloride was taken in CH2Cl2 (0.5mL) and added to a solution of the alcohol (15mg), pyridine (0.1ml), and 4,4-dimethylaminopyridine (1-2 crystals) in CH2Cl2 (0.250mL). After stirring the mixture for 16h at room temperature, the excess pyridine was removed by purging with N2 gas, and the residue was subjected to preparative thin-layer chromatography (silica gel, 10% EtOAc/hexane) to isolate the respective MTPA esters. 1H NMR analyses were carried out with the pure samples
  • 66
  • [ 39637-99-5 ]
  • [ 88206-46-6 ]
  • C31H29F3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With perdeuteriopyridine;Inert atmosphere; Sealed tube; General procedure: Two portions of compound 5 (0.5 mg/each) were dissolved in pyridine-d5 (0.55 mL) in two dried NMR tubes. (S)-(+)- or (R)- (-)-α-methoxy-α-(trifluoromethyl) phenylacetyl chloride (MTPA-Cl) (8 μL) was separately added into the NMR tubes under N2 gas protection. The NMR tubes were sealed and reacted overnight. After the reactions were completed, 1H NMR and 1H-1H COSY experiments of the (R)- and (S)-MTPA ester derivatives were recorded. The 1H NMR chemical shifts of the derivatives of 5 were assigned on the basis of 1H-1H COSY and 1H NMR spectra in C5D5N. 1H NMR spectra of (R)- and (S)-MTPA esters of 5 (400 MHz, pyridine-d5) are shown in the supplemental data.
With perdeuteriopyridine;Inert atmosphere; Sealed tube; General procedure: Two portions of compound 5 (0.5 mg/each) were dissolved in pyridine-d5 (0.55 mL) in two dried NMR tubes. (S)-(+)- or (R)- (-)-α-methoxy-α-(trifluoromethyl) phenylacetyl chloride (MTPA-Cl) (8 μL) was separately added into the NMR tubes under N2 gas protection. The NMR tubes were sealed and reacted overnight. After the reactions were completed, 1H NMR and 1H-1H COSY experiments of the (R)- and (S)-MTPA ester derivatives were recorded. The 1H NMR chemical shifts of the derivatives of 5 were assigned on the basis of 1H-1H COSY and 1H NMR spectra in C5D5N. 1H NMR spectra of (R)- and (S)-MTPA esters of 5 (400 MHz, pyridine-d5) are shown in the supplemental data.
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