Sodium Hydroxide → 4-((((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)(2-(dimethylamino)ethyl)amino)-4-oxobutanoic acid

HRID 405073Notes

Reaction equation

HRID 405073 reaction equation
[CH3:1][N:2]([CH3:57])[CH2:3][CH2:4][N:5]([CH2:14][C@:15]12[CH2:53][CH2:52][C@@H:51]([C:54]([CH3:56])=[CH2:55])[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([CH3:50])[C@@H:26]([CH2:27][CH2:28]2)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]2[CH:49]=[CH:48][C:40]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:39][CH:38]=2)=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[C:6](=[O:13])[CH2:7][CH2:8][C:9]([O:11]C)=[O:10].[OH-].[Na+]>O1CCOCC1>[C:44]([O:43][C:41]([C:40]1[CH:48]=[CH:49][C:37]([C:24]2[C:25]([CH3:36])([CH3:35])[C@H:26]3[C@:21]([CH3:50])([CH2:22][CH:23]=2)[C@@H:20]2[C@:29]([CH3:34])([C@@:30]4([CH3:33])[C@H:17]([CH2:18][CH2:19]2)[C@H:16]2[C@H:51]([C:54]([CH3:56])=[CH2:55])[CH2:52][CH2:53][C@:15]2([CH2:14][N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:57])[C:6](=[O:13])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:32][CH2:31]4)[CH2:28][CH2:27]3)=[CH:38][CH:39]=1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86676411tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((N-(2-(dimethylamino)ethyl)-4-methoxy-4-oxobutanamido)methyl)-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

Product 1

HCID 866764104-((((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)(2-(dimethylamino)ethyl)amino)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((N-(2-(dimethylamino)ethyl)-4-methoxy-4-oxobutanamido)methyl)-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 (53 mg, 0.068 mmol) in 1,4-dioxane (1 ml) was added NaOH (0.338 ml, 0.338 mmol). The mixture was heated to 75° C. for 3 h. The mixture was cooled to rt and was quenched with 1N HCl (3 ml) and extracted with dichloromethane (3×7 ml). The combined organic layers were dried with Na2SO4, were filtered, and concentrated under reduced pressure. The crude product was used in the next step with no additional purification. LCMS: m/e 771.6 (M+H)+, 2.70 min (method 6).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customwas quenched with 1N HCl (3 ml)
  3. extractionextracted with dichloromethane (3×7 ml)
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. filtrationwere filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was used in the next step with no additional purification
  8. customm/e 771.6 (M+H)+, 2.70 min (method 6)

Sources & evidence

ORD record
ord-2dfa880277c84b55a6a6f93d997e983a
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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