2-Pyrimidineacetic Acid → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyrimidin-2-yl)acetamido)-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

HRID 85603Notes

Reaction equation

HRID 85603 reaction equation
[NH2:1][C@:2]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:34])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.[N:41]1[CH:46]=[CH:45][CH:44]=[N:43][C:42]=1[CH2:47][C:48](O)=[O:49]>>[CH3:20][C@:17]12[C@@:16]3([CH3:21])[C@@H:7]([C@:8]4([CH3:34])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[CH:10][CH2:9]4)[CH2:6][CH2:5][C@@H:4]1[C@H:3]1[C@H:35]([C:38]([CH3:40])=[CH2:39])[CH2:36][CH2:37][C@:2]1([NH:1][C:48](=[O:49])[CH2:47][C:42]1[N:43]=[CH:44][CH:45]=[CH:46][N:41]=1)[CH2:19][CH2:18]2

Participants

3

Reactant 2

HCID 123670982-Pyrimidineacetic AcidHCID 68357865methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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)benzoate

Product 1

HCID 683581124-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyrimidin-2-yl)acetamido)-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

Procedure

The title compound was prepared from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-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)benzoate following the general procedure described for the parallel synthesis of C-17 amides above, using 2-pyrimidine acetic acid as the reacting carboxylic acid. LCMS: m/e 650.6 (M+H)+, 5.57 min (method 3). 1H NMR (599 MHz, <DMSO_CDCl3>) δ=8.78 (d, J=4.7 Hz, 2H), 7.88 (d, J=8.2 Hz, 2H), 7.29 (s, 1H), 7.22 (d, J=7.6 Hz, 2H), 5.28 (d, J=5.3 Hz, 1H), 4.75 (s, 1H), 4.62 (br. s., 1H), 3.93 (s, 1H), 3.82 (d, J=14.6 Hz, 1H), 2.77-2.72 (m, 1H), 2.63 (d, J=12.9 Hz, 1H), 2.40-2.32 (m, 1H), 2.16-2.04 (m, 1H), 2.00-1.81 (m, 2H), 1.73 (br. s., 2H), 1.71 (s, 3H), 1.67-1.52 (m, 4H), 1.50-1.39 (m, 7H), 1.36-1.20 (m, 7H), 0.99 (br. s., 6H), 0.98 (br. s., 3H), 0.93 (br. s., 3H), 0.93 (br. s., 3H).

Workup

  1. customm/e 650.6 (M+H)+, 5.57 min (method 3)

Sources & evidence

ORD record
ord-6081f1e79509424bb1636bc7e6fe8adc
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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