1-(Chloroacetyl)pyrrolidine → HCID 86676596, compound
Reaction equation
[CH3:1][N:2]([CH3:45])[C:3](=[O:44])[CH2:4][NH:5][C@:6]12[CH2:40][CH2:39][C@@H:38]([C:41]([CH3:43])=[CH2:42])[C@@H:7]1[C@@H:8]1[C@@:21]([CH3:24])([CH2:22][CH2:23]2)[C@@:20]2([CH3:25])[C@@H:11]([C@:12]3([CH3:37])[C@@H:17]([CH2:18][CH2:19]2)[C:16]([CH3:27])([CH3:26])[C:15]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1.Cl[CH2:47][C:48](N1CCCC1)=O>>[CH3:24][C@:21]12[C@@:20]3([CH3:25])[C@@H:11]([C@:12]4([CH3:37])[C@@H:17]([CH2:18][CH2:19]3)[C:16]([CH3:27])([CH3:26])[C:15]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:35][CH:36]=3)=[CH:14][CH2:13]4)[CH2:10][CH2:9][C@@H:8]1[C@H:7]1[C@H:38]([C:41]([CH3:43])=[CH2:42])[CH2:39][CH2:40][C@:6]1([NH:5][CH2:4][C:3](=[O:44])[N:2]1[CH2:1][CH2:48][CH2:47][CH2:45]1)[CH2:23][CH2:22]2Participants
Reactant 2
Product 1
Procedure
The title compound was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)-2-oxoethylamino)-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 using 2-chloro-1-(pyrrolidin-1-yl)ethanone as the alkylating reagent in Step 1. The product was isolated as a white solid (19 mg, 46%). LCMS: m/e 641.46 (M+H)+, 2.55 min (method 10). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.24 Hz, 2H), 5.38 (d, J=4.58 Hz, 1H), 4.89 (s, 1H), 4.76 (s, 1H), 4.43 (d, J=16.48 Hz, 1H), 3.99 (d, J=16.17 Hz, 1H), 3.73-3.42 (m, 4H), 3.15-2.86 (m, 1H), 2.41-1.19 (m, 26H), 1.79 (s, 3H), 1.28 (s, 3H), 1.14 (s, 3H), 1.10 (s, 3H), 1.03 (s, 3H), 1.00 (s, 3H).
Sources & evidence
- ORD record
- ord-a928ededcefd4b99b7423b0724862d6e
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846647B2
Reaction notes
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