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Sodium Hydroxide → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2,2-dimethoxyethylamino)-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)benzoic acid

HRID 85645
Notes
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Reaction equation

HRID 85645 reaction equation
[CH3:1][O:2][CH:3]([O:45][CH3:46])[CH2:4][NH:5][C@:6]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:7]1[C@@H:8]1[C@@:21]([CH3:24])([CH2:22][CH2:23]2)[C@@:20]2([CH3:25])[C@@H:11]([C@:12]3([CH3:38])[C@@H:17]([CH2:18][CH2:19]2)[C:16]([CH3:27])([CH3:26])[C:15]([C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1.[OH-].[Na+]>O1CCOCC1.CO>[CH3:1][O:2][CH:3]([O:45][CH3:46])[CH2:4][NH:5][C@:6]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:7]1[C@@H:8]1[C@@:21]([CH3:24])([CH2:22][CH2:23]2)[C@@:20]2([CH3:25])[C@@H:11]([C@:12]3([CH3:38])[C@@H:17]([CH2:18][CH2:19]2)[C:16]([CH3:27])([CH3:26])[C:15]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:36][CH:37]=2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68358150methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2,2-dimethoxyethylamino)-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 683581394-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2,2-dimethoxyethylamino)-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)benzoic acid
Yield 66.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2,2-dimethoxyethylamino)-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 (0.025 g, 0.040 mmol) in 1,4-dioxane (1 mL) was added NaOH (1N) (0.198 mL, 0.198 mmol). The mixture was heated to 85° C. After 6 h of heating, the mixture was cooled to rt, the reaction mixture was diluted with MeOH and was purified by prep HPLC. The fractions containing the expected product were combined and were concentrated under reduced pressure to give the title compound (17 mg, 0.026 mmol, 66.1% yield) as a clear film. LCMS: m/e 618.8 (M+H)+, 2.28 min (method 11). 1H NMR (500 MHz, CHLOROFORM-d) d ppm 7.99 (d, J=7.93 Hz, 2H), 7.20 (d, J=7.93 Hz, 2H), 5.28 (d, J=4.88 Hz, 1H), 5.12 (br. s., 1H), 4.72 (s, 1H), 4.58 (s, 1H), 4.53 (t, J=5.49 Hz, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 2.64-2.74 (m, 2H), 2.60 (dd, J=11.44, 6.56 Hz, 1H), 1.97-2.13 (m, 2H), 1.86-1.95 (m, 2H), 1.81 (dd, J=12.51, 8.24 Hz, 1H), 1.68 (s, 3H), 1.11 (s, 3H), 0.98 (s, 3H), 0.97 (br. s., 3H), 0.95-1.72 (m, 17H), 0.93 (br. s., 6H).

Workup

  1. temperatureAfter 6 h of heating
  2. temperaturethe mixture was cooled to rt
  3. customwas purified by prep HPLC
  4. additionThe fractions containing the expected product
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d1c1fe9f7844cb6b7a834907aba26f2
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846647B2

Reaction notes

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