Hydrochloric Acid → HCID 71597437, compound

HRID 405084Notes

Reaction equation

HRID 405084 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:53])[CH2:11][CH2:12][NH:13][CH2:14][C@:15]12[CH2:49][CH2:48][C@@H:47]([C:50]([CH3:52])=[CH2:51])[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([CH3:46])[C@@H:26]([CH2:27][CH2:28]2)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]2[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)=[O:4].[OH-].[Na+].O.Cl>O1CCOCC1.CO>[C:41]([C:40]1[CH:44]=[CH:45][C:37]([C:24]2[C:25]([CH3:36])([CH3:35])[C@H:26]3[C@:21]([CH3:46])([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:47]([C:50]([CH3:52])=[CH2:51])[CH2:48][CH2:49][C@:15]2([CH2:14][NH:13][CH2:12][CH2:11][C:10]([N:6]2[CH2:7][CH2:8][CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])=[O:53])[CH2:32][CH2:31]4)[CH2:28][CH2:27]3)=[CH:38][CH:39]=1)([OH:43])=[O:42]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 71597438HCID 71597438, compound

Product 1

HCID 71597437HCID 71597437, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-((S)-2-(methoxycarbonyl)pyrrolidin-1-yl)-3-oxopropylamino)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)benzoic acid (10 mg, 0.014 mmol) in dioxane (1 ml) and methanol (2 ml) was added 1N sodium hydroxide (0.08 ml, 0.08 mmol) and H2O (0.5 ml). The resulting mixture was stirred at rt for 45 h. The reaction mixture was neutralized with 1N HCl and concentrated in vacuo. The residue was purified by prep. HPLC to afford the title compound (8.5 mg, 85%). MS: m/e 713.5 (MH+), 1.68 min (method 2). 1H NMR (400 MHz, MeOD) δ ppm 0.95 (s, 3H) 0.97 (s, 3H) 1.04 (s, 3H) 1.08 (s, 3H) 1.18 (s, 3H) 1.73 (s, 3H) 0.87-1.86 (m, 20H) 1.99-2.10 (m, 4H) 2.15 (dd, J=17.32, 6.53 Hz, 1H) 2.24-2.33 (m, 1H) 2.52 (td, J=9.60, 4.14 Hz, 1H) 2.83-2.92 (m, 3H) 3.24-3.28 (m, 1H) 3.38 (t, J=6.15 Hz, 2H) 3.52-3.68 (m, 2H) 4.48 (dd, J=8.41, 3.39 Hz, 1H) 4.64 (s, 1H) 4.76 (d, J=1.76 Hz, 1H) 5.30 (dd, J=6.15, 1.63 Hz, 1H) 7.21 (d, J=8.53 Hz, 2H) 7.91 (d, J=8.28 Hz, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by prep

Sources & evidence

ORD record
ord-1fcc904587d94680a1b88129a8fd1db3
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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