Structure of 3471-10-1
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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. : | 3471-10-1 |
Formula : | C10H10O2 |
M.W : | 162.19 |
SMILES Code : | OC(=O)[C@@H]1C[C@H]1C1=CC=CC=C1 |
MDL No. : | MFCD00001292 |
InChI Key : | AHDDRJBFJBDEPW-DTWKUNHWSA-N |
Pubchem ID : | 237413 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
Resolution of racemate; | ±trans-2-phenylcyclopropanecarboxylic acid was separated into constituent enantiomers (Intermediate Y and Z) using chiral SFC. Intermediate Y: 1HNMR (300 MHz, CDC13) δ 1HNMR (300 MHz, CDC13) δ 7.35-7.09 (m, 5H), 2.61 (ddd, 1H), 1.91 (dq, 1H), 1.67 (q, 1H), 1.42 (dq, 1H). ESIMS m/z [M-H]+ 161.2. [a]D24 4 -259.546 (c 0.119, MeOH). Absolute stereochemistry assigned by comparison with literature (JMC 2000, p3923; JMC 2011, p957). Intermediate Z: 1HNMR (300 MHz, CDC13) δ 7.35-7.09 (m, 5H), 2.61 (ddd, 1H), 1.91 (dq, J = 4.8, 3.9, 1H), 1.67 (q, 1H), 1.42 (dq, 1H). ESIMS m/z [M-H]+ 161.2. [a]D245 +249.261 (c 0.102, MeOH). Absolute stereochemistry assigned by comparison with literature (JMC 2000, p3923; JMC 2011, p957). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Chiralcel AD-H; In hexane; isopropyl alcohol;Resolution of racemate;Purification / work up; | Enantiomers (R,2R)- and (15',25)-2-phenylcyclopropanecarboxylic acid (8A, and 8B, respectively) were separated from 1 gram of a commercially available racemic mixture on a Waters System using Chiralcel AD-H 250x2 lmm at a flow rate of 20mL/min in 96-4% Hexane:iPrOH. Each injection was 50 mg/mL. Only the first peak was separated out but the second and third peak eluted concurrently. The first peak, (lS,2S)-2- phenylcyclopropanecarboxylic acid (8B), and the third peak, (lR,2R)-2- phenylcyclopropanecarboxylic acid (8A), were in a 1 :1 ratio and composed the majority of mixture. The second peak is the cis diastereomers. The separation yielded 420 mg (41% recovery) for 8B, and 750 mg for the mixture of 8A and cis diastereomers. Optical rotation for the first peak, (15f,25)-2-phenylcyclopropanecarboxylic acid (8B), is +337 (c=0.761, CHCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With diphenyl phosphoryl azide; triethylamine; at 90℃; for 5.0h; | [0257] Into a 250-mL round-bottom flask, was placed (lR,2R)-2- phenylcyclopropanecarboxylic acid 5 (5 g, 30.83 mmol, 1.00 equiv), tert-butanol (100 mL), diphenyl phosphorazidate "DPPA" (8.5 g, 30.89 mmol, 1.00 equiv), TEA (3.1 g, 30.64 mmol, 1.00 equiv). The resulting solution was stirred for 5 hours at 90C in an oil bath. After the reaction was completed, it was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1: 10). The collected fractions were combined and concentrated under vacuum. This resulted in 5.2 g (72%) of tert-butyl (lR,2S)-2-phenylcyclopropylcarbamate as a yellow solid. |
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