1-methyl-D-Proline → HCID 71598491, compound

HRID 405092Notes

Reaction equation

HRID 405092 reaction equation
[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:33]([C:36]([CH3:38])=[CH2:37])[CH2:34][CH2:35][C@:5]1([CH2:39][NH:40][C:41]([C@@H:43]1[CH2:47][CH2:46][CH2:45][N:44]1[CH3:48])=[O:42])[CH2:4][CH2:3]2.CN1CCC[C@@H]1C(O)=O>>[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:32])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:21])([CH3:22])[C:14]([C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:33]([C:36]([CH3:38])=[CH2:37])[CH2:34][CH2:35][C@:5]1([CH2:39][NH:40][C:41]([C@H:43]1[CH2:47][CH2:46][CH2:45][N:44]1[CH3:48])=[O:42])[CH2:4][CH2:3]2

Participants

3

Reactant 2

HCID 8540341-methyl-D-ProlineHCID 71598490HCID 71598490, compound

Product 1

HCID 71598491HCID 71598491, compoundYield 37%

Procedure

The title compound was prepared in 37% yield following the procedure described above in the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(((S)-1-methylpyrrolidine-2-carboxamido)methyl)-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 150, using (R)-1-methylpyrrolidine-2-carboxylic acid as the reactant acid. MS: m/e 655.7 (MH+), 1.73 min (method 2). 1H NMR (400 MHz, MeOD) δ ppm 0.94 (s, 3H) 0.96 (s, 3H) 1.03 (s, 3H) 1.05 (s, 3H) 1.17 (s, 3H) 1.71 (s, 3H) 0.85-2.25 (m, 24H) 2.14 (dd, J=17.07, 6.27 Hz, 1H) 2.48-2.62 (m, 2H) 2.90 (s, 3H) 3.15-3.25 (m, 2H) 3.50-3.57 (m, 1H) 3.67-3.76 (m, 1H) 4.04 (t, J=8.16 Hz, 1H) 4.61 (s, 1H) 4.73 (d, J=2.01 Hz, 1H) 5.29 (dd, J=6.15, 1.63 Hz, 1H) 7.21 (d, J=8.28 Hz, 2H) 7.91 (d, J=8.28 Hz, 2H) 8.24 (t, J=5.90 Hz, 1H).

Workup

  1. customm/e 655.7 (MH+), 1.73 min (method 2)

Sources & evidence

ORD record
ord-98a0e764acfd45fe8188f36c5864e678
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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