Diisopropylethylamine → 4-(N-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl)sulfamoyl)benzoic acid

HRID 405095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405095
[NH2:1][CH2:2][C@:3]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:4]1[C@@H:5]1[C@@:18]([CH3:21])([CH2:19][CH2:20]2)[C@@:17]2([CH3:22])[C@@H:8]([C@:9]3([CH3:38])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:24])([CH3:23])[C:12]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1.Cl[S:46]([C:49]1[CH:57]=[CH:56][C:52]([C:53]([OH:55])=[O:54])=[CH:51][CH:50]=1)(=[O:48])=[O:47].CCN(C(C)C)C(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:32]([O:31][C:29]([C:28]1[CH:36]=[CH:37][C:25]([C:12]2[C:13]([CH3:24])([CH3:23])[C@H:14]3[C@:9]([CH3:38])([CH2:10][CH:11]=2)[C@@H:8]2[C@:17]([CH3:22])([C@@:18]4([CH3:21])[C@H:5]([CH2:6][CH2:7]2)[C@H:4]2[C@H:39]([C:42]([CH3:44])=[CH2:43])[CH2:40][CH2:41][C@:3]2([CH2:2][NH:1][S:46]([C:49]2[CH:50]=[CH:51][C:52]([C:53]([OH:55])=[O:54])=[CH:56][CH:57]=2)(=[O:48])=[O:47])[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)=[CH:26][CH:27]=1)=[O:30])([CH3:33])([CH3:34])[CH3:35]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 86676419tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aminomethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Produkt 1

HCID 866764184-(N-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl)sulfamoyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aminomethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (25 mg, 0.042 mmol) in DCM (2 ml) was added 4-(chlorosulfonyl)benzoic acid (9.19 mg, 0.042 mmol) and DIPEA (7.28 μl, 0.042 mmol). The resulting mixture was stirred for 48 h at rt. The mixture was diluted with 7 ml of sat. NaHCO3 and was extracted with dichloromethane (3×7 ml). The combined organic layers were dried with Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was used in the next step with no additional purification.

Aufarbeitung

  1. extractionwas extracted with dichloromethane (3×7 ml)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was used in the next step with no additional purification

Quellen und Nachweise

ORD-Eintrag
ord-6f0877c4bc0947d29eb7f0d5fe8f3ce8
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748415B2

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