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Hydrochloric Acid → (2S, 4S, 5S)-5-{N-[N-Morpholinoacetyl-3-(1-naphthyl)-L-alanyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-[2(S)-methylbutyl]hexanamide

HRID 2380097
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Reaktionsgleichung

Reaktionsgleichung von HRID 2380097
C(O[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C@@H:20]([OH:35])[CH2:21][C@@H:22]([C:31]([OH:34])([CH3:33])[CH3:32])[C:23]([NH:25][CH2:26][C@@H:27]([CH3:30])[CH2:28][CH3:29])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])(C)(C)C.Cl.[O:44]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]([NH:53][C@H:54](C(O)=O)[CH2:55][C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH:59]=[CH:58][CH:57]=2)=[O:52])[CH2:46][CH2:45]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>O1CCOCC1>[O:44]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]([NH:53][C@H:54]([C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:36][CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[C@@H:20]([OH:35])[CH2:21][C@@H:22]([C:31]([OH:34])([CH3:33])[CH3:32])[C:23]([NH:25][CH2:26][C@@H:27]([CH3:30])[CH2:28][CH3:29])=[O:24])=[O:17])[CH2:10][C:11]2[N:12]=[CH:13][S:14][CH:15]=2)=[O:7])[CH2:55][C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH:59]=[CH:58][CH:57]=2)=[O:52])[CH2:46][CH2:45]1
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Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 14989051(2S, 4S, 5S)-5-{N-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino}-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-[2(S)-methylbutyl]hexanamideHCID 14989052N-morpholinoacetyl-3-(1-naphthyl)-L-alanine

Produkt 1

HCID 14989053
(2S, 4S, 5S)-5-{N-[N-Morpholinoacetyl-3-(1-naphthyl)-L-alanyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-[2(S)-methylbutyl]hexanamide
Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 150 mg (0.25 mmoles) of (2S, 4S, 5S)-5-{N-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino}-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-[2(S)-methylbutyl]hexanamide (prepared as described in Example 1) in 5 ml of a 4N solution of hydrogen chloride in dioxane was stirred at room temperature for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and diethyl ether was added to the residue. The solvent was then again removed by distillation under reduced pressure. This operation was repeated in total three times, and then the final residue was dried under vacuum for 8 hours. The dried material was suspended in 10 ml of anhydrous tetrahydrofuran, and then 100 mg (0.29 mmoles) of N-morpholinoacetyl-3-(1-naphthyl)-L-alanine were added to the resulting suspension, followed by 0.04 ml (0.26 mmoles) of 95% diethyl cyanophosphate and 0.11 ml (0.79 mmoles) of triethylamine, all whilst ice-cooling and under an atmosphere of nitrogen. The mixture was then stirred for 8 hours, after which the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel thin layer chromatography (using a 10:1 by volume mixture of methylene chloride and methanol as eluent), to give 150 mg (yield 73%) of the title compound as white crystals, melting at 141°-143° C.

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure, and diethyl ether
  2. additionwas added to the residue
  3. customThe solvent was then again removed by distillation under reduced pressure
  4. dry with materialthe final residue was dried under vacuum for 8 hours
  5. temperatureall whilst ice-cooling and under an atmosphere of nitrogen
  6. stirringThe mixture was then stirred for 8 hours
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by silica gel thin layer chromatography (
  9. additionby volume mixture of methylene chloride and methanol as eluent),

Quellen und Nachweise

ORD-Eintrag
ord-8fc734ba012f475ba9f888d693288e4b
Quelldatensatz
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05364844

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