1-Iodopropane → HCID 67777513, compound

HRID 2405497Notes

Reaction equation

HRID 2405497 reaction equation
[C:1]([CH2:4][CH2:5][N:6]([CH2:50][CH3:51])[CH2:7][CH2:8][NH:9][C:10]([C@:12]12[CH2:46][CH2:45][C@@H:44]([C:47]([CH3:49])=[CH2:48])[C@@H:13]1[C@@H:14]1[C@@:27]([CH3:30])([CH2:28][CH2:29]2)[C@@:26]2([CH3:31])[C@@H:17]([C@:18]3([CH3:43])[C@@H:23]([CH2:24][CH2:25]2)[C:22]([CH3:33])([CH3:32])[C:21]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=2)=[CH:20][CH2:19]3)[CH2:16][CH2:15]1)=[O:11])([OH:3])=[O:2].I[CH2:53]CC>>[C:1]([CH2:4][CH2:5][N:6]([CH2:50][CH2:51][CH3:53])[CH2:7][CH2:8][NH:9][C:10]([C@:12]12[CH2:46][CH2:45][C@@H:44]([C:47]([CH3:49])=[CH2:48])[C@@H:13]1[C@@H:14]1[C@@:27]([CH3:30])([CH2:28][CH2:29]2)[C@@:26]2([CH3:31])[C@@H:17]([C@:18]3([CH3:43])[C@@H:23]([CH2:24][CH2:25]2)[C:22]([CH3:33])([CH3:32])[C:21]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=2)=[CH:20][CH2:19]3)[CH2:16][CH2:15]1)=[O:11])([OH:3])=[O:2]

Participants

3

Reactant 2

HCID 336431-IodopropaneHCID 54764882HCID 54764882, compound

Product 1

HCID 67777513HCID 67777513, compound

Procedure

The title compound was prepared following the method described above for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-((2-carboxyethyl)(ethyl)amino)ethylcarbamoyl)-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 (example 89). using 1-iodopropane as alkylating reagent. The product was isolated as a white solid (10 mg, 49%). LCMS: m/e 715.50 (M+H)+, 2.08 min (method 1). 1H NMR (500 MHz, Acetic Acid-d4) δ ppm 8.03 (d, J=7.93 Hz, 2H), 7.30 (d, J=8.24 Hz, 2H), 5.37 (d, J=4.58 Hz, 1H), 4.78 (s, 1H), 4.65 (s, 1H), 3.88-3.72 (m, 2H), 3.55 (t, J=7.02 Hz, 2H), 3.44 (q, J=6.51 Hz, 2H), 3.32-3.21 (m, 2H), 3.13 (td, J=11.22, 3.51 Hz, 1H), 2.97 (t, J=6.71 Hz, 2H), 2.55 (td, J=12.13, 3.81 Hz, 1H), 2.25-2.13 (m, 2H), 1.75 (s, 3H), 2.04-1.10 (m, 21H), 1.08 (s, 3H), 1.07 (s, 3H), 1.06 (s, 3H), 1.03 (t, J=5 Hz, 2H), 1.01 (s, 3H), 0.99 (s, 3H).

Sources & evidence

ORD record
ord-de879a878faf4d618815340db0962430
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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