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| | (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride Basic information |
| Product Name: | (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride | | Synonyms: | (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride;(3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydrochloride (Dil-HCl);Dolaisoleucine Hydrochloride (DIL-HCl);2-Methyl-2-propanyl (3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino) heptanoate hydrochloride (1:1);3R,4S,5S-tert-butyl 3-methoxy-5-methyl-4-;methylaminoheptanoatehydrochloride;DILTIAZEM HYDROCHLORIDE;CRD401; CRD-401;CRD 401;Dolproline intermediate1 | | CAS: | 120205-48-3 | | MF: | C14H30ClNO3 | | MW: | 295.85 | | EINECS: | | | Product Categories: | | | Mol File: | 120205-48-3.mol |  |
| | (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride Chemical Properties |
| storage temp. | Inert atmosphere,Room Temperature | | form | Solid | | color | White to off-white | | InChI | InChI=1/C14H29NO3.ClH/c1-8-10(2)13(15-6)11(17-7)9-12(16)18-14(3,4)5;/h10-11,13,15H,8-9H2,1-7H3;1H/t10-,11+,13-;/s3 | | InChIKey | JRXGCIIOQALIMZ-IPYRWZCONA-N | | SMILES | [C@H](NC)([C@@H](C)CC)[C@H](OC)CC(=O)OC(C)(C)C.Cl |&1:0,3,7,r| | | CAS DataBase Reference | 120205-48-3 |
| | (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride Usage And Synthesis |
| Uses | (3R,4S,5S)-3-Methoxy-5-methyl-4-(methylamino)heptanoic Acid 1,1-Dimethylethyl Ester is an β-methoxy-γ-amino acid component of dolastatin 10, an antineoplastic agent. | | Synthesis | General Procedure:(3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)(methyl)amino)-3-methoxy-5-methylheptanoate (13.37 g, 33.98 mmol, 1 eq.) was dissolved in methanol (134 mL, 0.1 M), concentrated hydrochloric acid (3.1 mL, 37.4 mmol, 1.1 eq.) was added, and 10% palladium carbon (50% wet, 0.1 wt%, 1.34 g, 3.40 mmol). The reaction mixture was hydrogenated under 45 psi hydrogen pressure for 3 hours. Upon completion of the reaction, the hydrogen was replaced with nitrogen, the catalyst was removed by filtration through diatomaceous earth, and the filtrate was concentrated under reduced pressure to afford tert-butyl (3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride (9.20 g, 92% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 9.65 (br s, 1H), 8.97 (br s, 1H), 3.98-4.04 (m, 1H), 3.40 (s, 3H), 3.06-3.13 (br m, 1H), 2.82 (br dd, J=6,5 Hz, 3H), 2.74-2.80 (m 1H), 2.68 (dd, half of ABX mode, J=16.3,4.2 Hz, 1H), 2.00-2.10 (br m, 1H), 1.73-1.84 (m, 1H), 1.46 (s, 9H), 1.38-1.45 (m, 1H), 1.13 (d, J=7.0 Hz, 3H), 0.99 (t, J= 7.4 Hz, 3H). | | References | [1] Patent: WO2013/72813, 2013, A2. Location in patent: Page/Page column 117 |
| | (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride Preparation Products And Raw materials |
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