Oxaceprol synthesis
- Product Name:Oxaceprol
- CAS Number:33996-33-7
- Molecular formula:C7H11NO4
- Molecular Weight:173.17
Yield: 70%
Reaction Conditions:
in water at 40 - 50; for 3 h;
Steps:
7 Acetylation of Trans-4-Hydroxy-L-Proline
To stirred suspension of 4-Hydroxy-L-proline (131 g) in distilled water (300 ml), acetic anhydride (110 ml) was added dropwise over 1 h, slowly the temperature of the reaction mass was increased to 50° C. After addition, the reaction mixture was maintained at 40-50° C. for 2 h. After completion of reaction, acetic acid and water are evaporated under vacuum. Product obtained as viscous syrup which was triturated with acetonitrile to give product as white solid (116 g, yield 70%). (0220) 1H NMR (300 MHz, DMSO): δ 1.943 (m, 3H), 2.05-2.08 (m, 1H), 3.33-3.37 (m, 2H), 3.57-3.62 (m, 1H), 4.16-4.21 (m, 1H), 4.31-4.50 (m, 1H), 5.14 (brs, 1H) D2O exchangeable, 12.37 (brs, 1H) D2O exchangeable, MS (m/z): 174.54 [M-H]+, SOR: [α]D25-105° (c=4, water), (0221) Melting Point:-127-132° C.)
References:
Glenmark Pharmaceuticals Limited;Kadam, Suresh Mahadev;Kansagra, Bipin Parsottam;Kale, Ramchandran Vishnue;Patil, Jayant Prakashrao;Yemireddy, Venkataramana Reddy;Bhadane, Shailendra Nilkanth;Chaudhar, Uddhav Popat;Patil, Ulhas Digambar;Bhirud, Shekhar Bhaskar US9518048, 2016, B2 Location in patent:Page/Page column 28
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1000210-73-0
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