2,2-Dimethylsuccinic anhydride → HCID 66858177, compound

HRID 2179819Notes

Reaction equation

HRID 2179819 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:49])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:48])[CH2:9][CH2:10][C@@:11]3([C:27]([NH:29][CH2:30][CH2:31][CH:32]4[O:37][C:36]([CH3:39])([CH3:38])[O:35][CH:34]([CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:33]4)=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:51])[CH3:50].CC1C=CN=C(N)C=1C.[CH3:61][C:62]1([CH3:69])[CH2:66][C:65](=[O:67])[O:64][C:63]1=[O:68]>N1C=CC=CC=1.C(OCC)(=O)C>[C:44]([O:43][C:41](=[O:42])[CH2:40][CH:34]1[O:35][C:36]([CH3:38])([CH3:39])[O:37][CH:32]([CH2:31][CH2:30][NH:29][C:27]([C@:11]23[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]2[C@@H:13]2[C@@:8]([CH3:48])([CH2:9][CH2:10]3)[C@@:7]3([CH3:49])[C@@H:16]([C@:17]4([CH3:20])[C@@H:4]([CH2:5][CH2:6]3)[C:3]([CH3:51])([CH3:50])[C@@H:2]([O:1][C:65](=[O:67])[CH2:66][C:62]([CH3:69])([CH3:61])[C:63]([OH:68])=[O:64])[CH2:19][CH2:18]4)[CH2:15][CH2:14]2)=[O:28])[CH2:33]1)([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 3

HCID 870672,2-Dimethylsuccinic anhydrideHCID 110078842-Amino-3,4-dimethylpyridineHCID 50924701HCID 50924701, compound

Product 1

HCID 66858177HCID 66858177, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 2-(6-(2-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxamido)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (Example 79, 0.5 g, 0.80 mmol) in pyridine (5 ml), dimethyl amino pyridine (0.2 g, 1.6 mmol) and 3,3-dimethyldihydrofuran-2,5-dione (0.82 ml) were added. Contents were refluxed for about 16 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml). The organic layer was washed with 5% aqueous HCl, water followed by brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% MeOH in DCM as eluent to furnish the title compound (0.25 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.95-1.16 (m, 19H); 1.23-1.78 (m, 23H); 2.15-2.59 (m, 11H); 2.77-3.58 (m, 16H); 4.33-4.70 (m, 4H); 5.58-5.60 (s, 1H); 5.78-5.80 (s, 1H); 7.44-7.47 (s, 1H); ES Mass: 806 [M+Na].

Workup

  1. temperatureContents were refluxed for about 16 hours
  2. customAfter completion of the reaction
  3. washThe organic layer was washed with 5% aqueous HCl, water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-913c75439d854bc98a493dac8c63f3e9
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…