Sodium Hydroxide → HCID 78321327, compound

HRID 1773040Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl 1-((tert-butoxycarbonyl)amino)-2-((E)-2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-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)vinyl)cyclopropanecarboxylate (12 mg, 0.015 mmol) in dioxane (2 mL) and MeOH (1 mL) was added 1N NaOH (1 mL, 1 mmol). The mixture was stirred at 25° C. for 2 h. The crude product was purified by prep HPLC (method 4) to give 1-((tert-butoxycarbonyl)amino)-2-((E)-2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-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)vinyl)cyclopropanecarboxylic acid as a white solid (1 mg, 8.63%). MS: m/e 796.55 (M+H)+, 2.57 min (method 2). 1H NMR (400 MHz, METHANOL-d4) δ 7.37-5.41 (m, 2H), 5.36-5.10 (m, 1H), 4.73 (br. s., 1H), 4.57 (br. s., 1H), 3.19-2.97 (m, 8H), 2.80-2.62 (m, 4H), 2.58-2.41 (m, 1H), 2.36-1.78 (m, 7H), 1.72 (s, 3H), 1.69-1.21 (m, 25H), 1.16 (m, 6H), 1.09-1.00 (m, 6H), 0.98-0.82 (m, 6H).

Workup

customThe crude product was purified by prep HPLC (method 4)

Sources & evidence

ORD record: ord-f6e38218018241d49d487382f458b84f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249180B2

Reaction notes

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