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Structure of 1312161-65-1

Chemical Structure| 1312161-65-1

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Product Details of [ 1312161-65-1 ]

CAS No. :1312161-65-1
Formula : C11H17NO4
M.W : 227.26
SMILES Code : O=C(C1=CC[C@H](NC(OC(C)(C)C)=O)C1)O
MDL No. :MFCD19381768

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Application In Synthesis of [ 1312161-65-1 ]

* 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 [ 1312161-65-1 ]

[ 1312161-65-1 ] Synthesis Path-Downstream   1~4

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YieldReaction ConditionsOperation in experiment
EXAMPLE 3: Epimerisation of (1 S,4R)-methyl 4-(te/f-butoxycarbonyl)amino cyclopent-2-enecarboxylate, 11.11 11+12 13A methanol solution of 11 (10 L, containing about 23.63 mol) is cooled to - 2C. A solution of sodium methoxide (127.6 g, 2.36 mol) in methanol (700 mL) is added over 30 minutes, at a rate that maintains the reaction temperature at 00C or less. After 50 minutes, gas chromatography (GC) analysis indicates a product distribution of 43% compound 12, 54% compound 11 , and 3% compound 13.Acetic acid (140 mL) is added over 5 minutes, the mixture is allowed to warm to 100C, then the mass is concentrated. After 7 L of solvent has been removed, the concentrated mixture is diluted with water (2 L) and MTBE (10 L).The aqueous layer is extracted with further MTBE (1 L). The combined organic layers are concentrated to give the products 11+12+13 in a MTBE solution, with a total volume of 7.5 L.A sample (2 mL) is removed from the bulk and concentrated further, and this is found to contain 1.5 g of product and therefore 7.5 L should contain 5.625 kg, (99% mass recovery).GC analysis shows the material to be 44% compound 12, 52% compound11 , and 4% compound 13.trans Diastereoismer 12; 1H NMR (400MHz, MeOH): delta 5.91 -5.87 (1 H, m),5.85-5.81 (1 H, m), 4.74 (1 H, brs), 3.75-3.72 (1 H, m) 3.66, (3H, s), 2.60-2.49 (1 H, m), 1.89-1.78 (1 H, m), 1.46 (9H, s). cis Diastereoismer 11 ; 1H NMR (400MHz, MeOH): delta 5.91 -5.87 (1 H, m), 5.85-5.81 (1 H, m), 4.65 (1 H, brs), 3.72, (3H, s), 3.57-3.52 (1 H, m), 2.60-2.49 (1 H, m), 1.89-1.78 (1 H, m), 1.46 (9H, s). EXAMPLE 4: Ester hydrolysis.A solution of a mixture of methyl esters 11+12+13 in MTBE (3.5 L, containing about 11.0 mol) is diluted with methanol (4 L) under N2, then cooled to -3.5C (jacket temperature -5C). A solution of lithium hydroxide monohydrate (508 g, 12.08 mol) in water (2.5 L) is added over 5.5 hours with the reaction temperature being kept below 2C at all times during the addition. Once the addition is complete, the mass is stirred for at 2C for 30 minutes, then at 100C for 16 hours.The mass is neutralised with 6 M HCI and concentrated. After 4 L of solvent has been removed, the concentrated mixture is acidified to pH 3 by the addition of further 6M HCI. The acidic mixture is extracted with ethyl acetate (10 L, then 2.5 L), and the combined organics are washed with brine (2*1.5 L), then concentrated. Toluene (2*2.5 L) is added during the concentration to aid the removal of water. The products 14+15+16 are recovered as an off white solid (2.67 kg, 94% yield).trans Diastereoismer 15; 1H NMR (400MHz, MeOH): delta 5.93-5.90 (1 H, m), 5.84-5.83 (1 H, m), 4.75 (1 H, brs), 3.72-3.67 (1 H, m), 2.59-2.49 (1 H, m), 1.90-1.78 (1 H, m), 1.45 (9H, s).cis Diastereoismer 14; 1H NMR (400MHz, MeOH): delta 5.93-5.90 (1 H, m), 5.84-5.83 (1 H, m), 4.67 (1 H, brs), 3.52-3.48 (1 H, m), 2.59-2.49 (1 H, m), 1.90-1.78 (1 H, m), 1.45 (9H, s).
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