Sodium Hydroxide → HCID 67952361, compound

HRID 406899Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([CH3:42])([CH3:41])[C@H:13]3[C@:30]([CH3:33])([CH2:31][CH:32]=2)[C@@H:29]2[C@:16]([CH3:40])([C@@:17]4([CH3:39])[C:26](=[CH:27][CH2:28]2)[C@H:25]2[C@:20]([C:36]([OH:38])=[O:37])([CH2:21][CH2:22][C@@H:23]([CH3:35])[C@@H:24]2[CH3:34])[CH2:19][CH2:18]4)[CH2:15][CH2:14]3)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>O1CCOCC1.CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([CH3:42])([CH3:41])[C@H:13]3[C@:30]([CH3:33])([CH2:31][CH:32]=2)[C@@H:29]2[C@:16]([CH3:40])([C@@:17]4([CH3:39])[C:26](=[CH:27][CH2:28]2)[C@H:25]2[C@:20]([C:36]([OH:38])=[O:37])([CH2:21][CH2:22][C@@H:23]([CH3:35])[C@@H:24]2[CH3:34])[CH2:19][CH2:18]4)[CH2:15][CH2:14]3)=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

Conditions

Temperature: 65 °C

Procedure

Saponification of the intermediates A6 was conducted as followed: to a solution of (1S,2R,4aS,6aS,6bR,8aR,12aS,12bR,14bS)-10-(4-(methoxycarbonyl)phenyl)-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-octadecahydropicene-4-a-carboxylic acid (intermediate A6) (20 mg, 0.035 mmol) in a mixture of dioxane (1 mL) and methanol (0.5 mL) was added a 1N solution of NaOH (0.5 mL, 0.5 mmol). The mixture was warmed to 65° C. for 2 h. The crude product was further purified by preparative HPLC(YMC Combiprep ODS 30×50 mm S5 column) eluted with gradient mixture of MeOH/water/TFA. The desired fractions were combined, evaporated to afford the title compound (12 mg, 61%).

Workup

customThe crude product was further purified by preparative HPLC(YMC Combiprep ODS 30×50 mm S5 column)
washeluted with gradient mixture of MeOH/water/TFA
customevaporated

Sources & evidence

ORD record: ord-f511baa1c6ef4369970a932c52e1922e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754068B2

Reaction notes

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