Hydrochloric Acid → HCID 86575413, compound

HRID 1401004Notes

Reaction equation

[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:42])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH2:41][C:25]5([CH2:28][C:27]([C:35]([O:37]C(C)C)=[O:36])([C:29]([O:31]C(C)C)=[O:30])[CH2:26]5)[CH:24]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:43]([C:46]([CH3:48])=[CH2:47])[CH2:44][CH2:45][C@:5]1([NH:49][CH2:50][CH2:51][N:52]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[S:53]([C:56]([F:59])([F:58])[F:57])(=[O:55])=[O:54])[CH2:4][CH2:3]2.[OH-].[Na+].Cl>O1CCOCC1.CO>[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:42])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:21])([CH3:22])[C:14]([C:23]3[CH2:41][C:25]5([CH2:26][C:27]([C:35]([OH:37])=[O:36])([C:29]([OH:31])=[O:30])[CH2:28]5)[CH:24]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:43]([C:46]([CH3:48])=[CH2:47])[CH2:44][CH2:45][C@:5]1([NH:49][CH2:50][CH2:51][N:52]([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[S:53]([C:56]([F:57])([F:58])[F:59])(=[O:55])=[O:54])[CH2:4][CH2:3]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of diisopropyl 6-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((2-(1,1,1-trifluoro-N-phenylmethylsulfonamido)ethyl)amino)-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)spiro[3.3]hept-5-ene-2,2-dicarboxylate (15 mg, 0.016 mmol) in dioxane (2 mL) and MeOH (1 mL) was added 1N NaOH (1 mL, 1 mmol). The mixture was stirred at 50° C. for 3 h. The mixture was neutralized by 1N HCl (1 mL) to pH ˜6 and solids formed were collected by filtration. The crude product was purified by preparative HPLC using method 14 to give 6-((1R,3 aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((2-(1,1,1-trifluoro-N-phenylmethylsulfonamido)ethyl)amino)-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)spiro[3.3]hept-5-ene-2,2-dicarboxylic acid in 42% yield as a solid. MS: m/e 841.5 (M+H)+, 2.52 min (method 4). 1H NMR (400 MHz, METHANOL-d4) δ 7.52-7.43 (m, 5H), 5.93 (s, 1H), 5.56-5.52 (m, 1H), 4.72 (d, J=1.8 Hz, 1H), 4.60 (s, 1H), 3.99 (s., 2H), 2.77-2.65 (m, 4H), 2.63-2.51 (m, 5H), 2.15 (dd, J=17.8, 6.5 Hz, 1H), 1.92-1.83 (m, 2H), 1.78-0.94 (m, 19H), 1.69 (s, 3H), 1.16 (s, 3H), 1.11 (s, 3H), 1.09 (s, 3H), 0.98 (s, 3H), 0.87 (s, 3H). 19F NMR (376 MHz, METHANOL-d4) δ −75.37 (s., 3F).

Workup

customformed
filtrationwere collected by filtration
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-6f80cd08edc440b8bf895882c8b31c8e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906889B2

Reaction notes

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