Tetrahydrofuran → HCID 50924997, compound

HRID 2179782Notes

Reaction equation

HRID 2179782 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:62])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:61])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:60])[NH:31][C@H:32]([C@H:40]([OH:59])[CH2:41][N:42]4[C@H:51]([C:52](=[O:58])[NH:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:50][C@H:49]5[C@H:44]([CH2:45][CH2:46][CH2:47][CH2:48]5)[CH2:43]4)[CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:64])[CH3:63])(=O)C.C1COCC1.[OH-].[Na+]>CO>[C:54]([NH:53][C:52]([C@@H:51]1[CH2:50][C@H:49]2[C@H:44]([CH2:45][CH2:46][CH2:47][CH2:48]2)[CH2:43][N:42]1[CH2:41][C@@H:40]([OH:59])[C@@H:32]([NH:31][C:30]([C@:14]12[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]1[C@@H:16]1[C@@:11]([CH3:61])([CH2:12][CH2:13]2)[C@@:10]2([CH3:62])[C@@H:19]([C@:20]3([CH3:23])[C@@H:7]([CH2:8][CH2:9]2)[C:6]([CH3:63])([CH3:64])[C@@H:5]([OH:4])[CH2:22][CH2:21]3)[CH2:18][CH2:17]1)=[O:60])[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:58])([CH3:55])([CH3:56])[CH3:57]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 50924996HCID 50924996, compound

Product 1

HCID 50924997HCID 50924997, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((2S,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-phenylbutan-2-ylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 29, 0.5 g) in MeOH:THF (8:8 ml) and cooled the contents to 0° C. then sodium hydroxide (0.12 g in 4 ml water) was added and the contents were stirred for about 6 hours at room temperature, and the completion of the reaction was monitored by TLC. The reaction mixture was evaporated under reduced pressure, the residue was taken in water and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% methanol in DCM as eluent to furnish the title compound (0.34 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.57-0.97 (m, 19H); 1.18-1.21 (m, 8H); 1.25-1.41 (m, 12H); 1.49-1.62 (m, 8H); 1.65-1.82 (m, 10H); 1.85-1.98 (m, 4H); 2.56-2.69 (m, 2H); 2.88-3.06 (m, 3H); 3.29-3.38 (m, 1H); 3.89-3.90 (m, 1H); 4.25-4.70 (m, 4H); 5.78 (s, 1H); 6.12-6.15 (d, J=9 Hz, 1H); 7.19-7.29 (m, 6H); ES Mass: 839 (100%), [M+1] 840.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ffad5c493a6144cc82f644bcc7d5d19d
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…