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CAS No. : | 69716-04-7 | MDL No. : | MFCD05273635 |
Formula : | C10H8O4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZEMXZWJZCWCPBM-UHFFFAOYSA-N |
M.W : | 192.17 | Pubchem ID : | 2110915 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
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 hydrogen;dichloro [(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)-N,N-dimethylformamide complex; In methanol; at 35℃; under 7500.75 Torr; for 15h;Autoclave; | Example 5Synthesis of [ (3S) -6-hydroxy-2, 3-dihydro-l-benzofuran-3- yl] acetic acid (S) -2-amino-l, 1-diphenylpropan-l-ol salt; [0396] [0397]( 6-Hydroxy-l-benzofuran-3-yl) acetic acid (25 g) ,dichloro[ (+)-l,2-bis( (2R, 5R)-2, 5- diisopropylphosphorano) benzene] ruthenium (II)-N,N- dimethylformamide complex (19.1 mg) and (S) -2-amino-l, .1- diphenylpropan-l-ol (29.5 g) were weighted in an autoclave and substituted with argon. Dehydrated methanol (250 mL) was added and the mixture was purged with hydrogen, pressurized under a hydrogen pressure (1.0 MPa) , and reacted at 35C for 15 hr.The reaction mixture was concentrated under reduced pressure, methanol (109 mL) and N, -dimethylformamide (27 mL) were added, and the mixture was dissolved by heating at 50C. Isopropyl ether (200 mL) was added dropwise at 60C, seed crystal was added, and isopropyl ether (369 mL) was added dropwise. The mixture was cooled to room temperature, stirred for 4 hr and stirred for 1 hr under ice-cooling, and the solid wascollected by filtration. The solid was dried at 60C under reduced pressure to give the title compound (38.98 g) . 99.8%de. XH NMR (500 MHz, DMSO-d6) : delta 0.85-0.92 (m, 1H) , 2.36 (dd,J=14.19 Hz), 2.59 (dd, J=16.24, 2.68 Hz, 1H) , 3.55-3.65 (m, 1H), 4.13 (dd, J=8.83 Hz, 1H) , 4.64 (t, J=8.83 Hz, 1H) , 6.16 (d, J=2.21 Hz, 1H) , 6.23 (dd, J=8.20, 2.21 Hz, 1H) , 6.93-7.00 (m, 1H), 7.09-7.21 (m, 2H) , 7.22-7.35 (m, 4H) , 7.51 (d, J=7.57 Hz, 2H) , 7.63 (dd, J=8.20 Hz, 2H)(high performance liquid chromatography conditions)column: CHIRALPAK AD-H (manufactured by DAICEL CHEMICALINDUSTRIES, LTD.)mobile phase: normal hexane/ethanol/trifluoroacetic acid (volume ratio: 90/10/0.1)flow rate: 1.0 mL/mindetection: UV 220 nmtemperature: 30C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethyl acetate; at 60℃; for 1h; | Reference Example 3Synthesis of ( 6-hydroxy-l-benzofuran-3-yl) acetic acid (S)-2- amino-1, 1-diphenylpropan-l-ol salt; 0399][0400]( 6-Hydroxy-l-benzofuran-3-yl) acetic acid (25.00 g) and (S) -2-amino-l, 1-diphenylpropan-l-ol (29.57 g) were added to ethyl acetate (175 mL) , and the mixture was dissolved by stirring at 60C. After allowing to cool to room temperature, isopropyl ether (200 mL) was added, and the mixture wasstirred for 1 hr. The solid was collected by filtration, and washed with a mixed solvent (1:1, 100 mL) of ethyl acetate- isopropyl ether. The solid was dried under reduced pressure at 50C to give the title compound (53.81 g) .? NMR (500 MHz, DMSO-d6) : delta 0.86 (d, J=5.67 Hz, 3H) , 3.51(br.s., 2H) , 4.06-4.16 (m, 1H) , 6.72 (dd, J=8.35, 2.05 Hz, 1H) , 6.86 (d, J=1.89 Hz, 1H) , 7.10-7.15 (m, 2H) , 7.15-7.37 (m, 5H) , 7.49 (dd, J=8.35, 1.42 Hz, 2H) , 7.58-7.65 (m,3H) |
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