참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 반응물 | 3-hydroxy-1,2,3-benzotriazin-4(3H)-one | HCID 73026 | — |
| 반응물 | (3Z)-3-[(2E)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylcyclohexan-1-ol | HCID 5281010 | — |
| 반응물 | (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide | HCID 9865804 | — |
| 반응물 | (S)-4-Amino-4-oxo-2-(((quinolin-2-yl)carbonyl)amino)butanoic acid | HCID 11044384 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | Saquinavir | HCID 441243 | 80.2% |
반응 단계
A solution of 287 mg of N-(2-quinolylcarbonyl)-L-asparagine and 401 mg of 2-[3(S)-amino-2(R)-hydroxy-4 -phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide in 3 ml of tetrahydrofuran was cooled to-10° C. and 163 mg of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one and 220 mg of dicyclohexylcarbodiimide were added. The mixture was stirred at-10° C. for 2 hours and at 20° C. for 16 hours, then diluted with ethyl acetate and filtered. The filtrate was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution and then evaporated. The residue was chromatographed on silica gel using 4% (by volume) methanol in dichloromethane for the elution to give 537 mg of N-tert.butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-asparaginyl]amino]butyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide as a white solid: MS: m/e 671 [M+H]+.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US05580999 |
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| 출처 데이터셋 | uspto-grants-1996_12 |
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| ORD ID | ord-b54199518e364631bdcd9360d9c31414 |
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| 출처 메모 | uspto-grants-1996_12 |
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