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Hydrochloric Acid → ({[(14-Cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-yl)carbonyl]amino}sulfonyl)acetic acid

HRID 1714000
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1714000
C[O:2][C:3](=[O:39])[CH2:4][S:5]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[C:15]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[C:16]3[C:23]4[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=4[CH2:21][N:20]([CH3:30])[CH2:19][CH2:18][N:17]3[C:31]=2[CH:32]=1)=[O:10])(=[O:7])=[O:6].O.[OH-].[Na+].Cl>O1CCOCC1>[CH:33]1([C:15]2[C:14]3[CH:13]=[CH:12][C:11]([C:9]([NH:8][S:5]([CH2:4][C:3]([OH:39])=[O:2])(=[O:7])=[O:6])=[O:10])=[CH:32][C:31]=3[N:17]3[CH2:18][CH2:19][N:20]([CH3:30])[CH2:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=4[C:16]=23)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 11613717HCID 11613717, Verbindung

Produkt 1

HCID 42640441({[(14-Cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-yl)carbonyl]amino}sulfonyl)acetic acidAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of methyl({[(14-cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-yl)carbonyl]amino}sulfonyl)acetate (from example 5) in dioxane (0.04 M) was added an equal volume of water and 4 eq of NaOH (1 N aqueous solution). The reaction was stirred vigorously at RT for 1 h. The reaction was acidified with aqueous HCl (1 N) and reduced in vacuo to remove dioxane. The resultant aqueous slurry was diluted with MeCN and water and freeze dried to leave a white powder. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (72%).

Aufarbeitung

  1. customto remove dioxane
  2. additionThe resultant aqueous slurry was diluted with MeCN and water and freeze
  3. customdried
  4. customto leave a white powder
  5. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  6. additionFractions containing the pure compound
  7. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-5c9dd2bed41b4fffabfe682f6d29ca11
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07795247B2

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