Hydrochloric Acid → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(3-(methylamino)propylcarbamoyl)-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

HRID 2405477Notes

Reaction equation

HRID 2405477 reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][CH2:11][NH:12][C:13]([C@:15]12[CH2:50][CH2:49][C@@H:48]([C:51]([CH3:53])=[CH2:52])[C@@H:16]1[C@@H:17]1[C@@:30]([CH3:33])([CH2:31][CH2:32]2)[C@@:29]2([CH3:34])[C@@H:20]([C@:21]3([CH3:47])[C@@H:26]([CH2:27][CH2:28]2)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]2[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=2)=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)=[O:14])=O)(C)(C)C.Cl>>[CH3:33][C@:30]12[C@@:29]3([CH3:34])[C@@H:20]([C@:21]4([CH3:47])[C@@H:26]([CH2:27][CH2:28]3)[C:25]([CH3:35])([CH3:36])[C:24]([C:37]3[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=3)=[CH:23][CH2:22]4)[CH2:19][CH2:18][C@@H:17]1[C@H:16]1[C@H:48]([C:51]([CH3:53])=[CH2:52])[CH2:49][CH2:50][C@:15]1([C:13](=[O:14])[NH:12][CH2:11][CH2:10][CH2:9][NH:8][CH3:6])[CH2:32][CH2:31]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67777052HCID 67777052, compound

Product 1

HCID 67773691methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(3-(methylamino)propylcarbamoyl)-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

Procedure

A vial containing methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(tert-butoxycarbonyl(methyl)amino)propylcarbamoyl)-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 (122 mg, 0.164 mmol) was diluted with HCl (4M in dioxane) (3 mL, 12.00 mmol). The mixture was stirred at rt. After 1.5 h of stirring at rt, LC/MS indicated the reaction was complete. The mixture was concentrated under reduced pressure. The crude product was carried forward to the next step with no additional purification. LCMS: m/e 641.5 (M−H)−, 2.73 min (method 3).

Workup

  1. stirringAfter 1.5 h of stirring at rt
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe crude product was carried forward to the next step with no additional purification
  4. customm/e 641.5 (M−H)−, 2.73 min (method 3)

Sources & evidence

ORD record
ord-f45d9579fb5646db81384e736e615790
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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