CN103408547B - 替诺福韦中间体(r)-1-(6-氨基嘌呤-9-基)-2-丙醇的制备方法 - Google Patents
替诺福韦中间体(r)-1-(6-氨基嘌呤-9-基)-2-丙醇的制备方法 Download PDFInfo
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- CN103408547B CN103408547B CN201310291885.0A CN201310291885A CN103408547B CN 103408547 B CN103408547 B CN 103408547B CN 201310291885 A CN201310291885 A CN 201310291885A CN 103408547 B CN103408547 B CN 103408547B
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- propyl alcohol
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- MJZYTEBKXLVLMY-RXMQYKEDSA-N (2r)-1-(6-aminopurin-9-yl)propan-2-ol Chemical compound N1=CN=C2N(C[C@H](O)C)C=NC2=C1N MJZYTEBKXLVLMY-RXMQYKEDSA-N 0.000 title abstract description 4
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- OFCBNMYNAHUDGE-UHFFFAOYSA-N 2-chloro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=C(Cl)N=C1 OFCBNMYNAHUDGE-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
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- CEXCTVLIYVFPCN-SCSAIBSYSA-N (2R)-1-[(6-chloro-5-nitropyrimidin-4-yl)amino]propan-2-ol Chemical compound O[C@@H](CNC1=NC=NC(=C1[N+](=O)[O-])Cl)C CEXCTVLIYVFPCN-SCSAIBSYSA-N 0.000 abstract 1
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- 238000009776 industrial production Methods 0.000 abstract 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- JFVZFKDSXNQEJW-CQSZACIVSA-N tenofovir disoproxil Chemical compound N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N JFVZFKDSXNQEJW-CQSZACIVSA-N 0.000 description 4
- 208000000419 Chronic Hepatitis B Diseases 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
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- RUOJZAUFBMNUDX-GSVOUGTGSA-N (4r)-4-methyl-1,3-dioxolan-2-one Chemical compound C[C@@H]1COC(=O)O1 RUOJZAUFBMNUDX-GSVOUGTGSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- 229940126656 GS-4224 Drugs 0.000 description 1
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- 241000700721 Hepatitis B virus Species 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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Abstract
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CN201310291885.0A CN103408547B (zh) | 2013-07-12 | 2013-07-12 | 替诺福韦中间体(r)-1-(6-氨基嘌呤-9-基)-2-丙醇的制备方法 |
PCT/CN2014/081717 WO2015003589A1 (zh) | 2013-07-12 | 2014-07-07 | 替诺福韦及其中间体的制备方法 |
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CN201310291885.0A CN103408547B (zh) | 2013-07-12 | 2013-07-12 | 替诺福韦中间体(r)-1-(6-氨基嘌呤-9-基)-2-丙醇的制备方法 |
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CN104710424B (zh) * | 2013-12-11 | 2017-03-01 | 河南师范大学 | (r)‑(+)‑9‑(2‑羟丙基)腺嘌呤的制备方法 |
CN106588932B (zh) * | 2016-12-20 | 2018-08-17 | 郑州泰丰制药有限公司 | 一种替诺福韦中间体的制备方法 |
CN108285471A (zh) * | 2018-03-16 | 2018-07-17 | 安徽华昌高科药业有限公司 | 一种替诺福韦的制备方法 |
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Non-Patent Citations (1)
Title |
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Kinetic resolution of terminal epoxides via highly regisoselective and enantioselective ring opening with TMSN3. An efficient, catalytic route to 1,2-amino alcohols.;Jay F. Larrow et al.;《J.Am.Chem.Soc.》;19961231;第118卷;7420-7421 * |
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