Ethyl Acetate → HCID 50924548, compound

HRID 2179775Notes

Reaction equation

HRID 2179775 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([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([C:27]([OH:29])=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:33])[CH3:32].[CH3:34][CH2:35][O:36][C:37]([CH3:39])=[O:38]>N1C=CC=CC=1>[CH2:35]([O:36][C:37]([C@@H:39]1[CH2:32][C@H:3]([C:2]([O:1][C@H:2]2[CH2:19][CH2:18][C@@:17]3([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]4([CH3:31])[C@@H:16]3[CH2:15][CH2:14][C@H:13]3[C@@:8]4([CH3:30])[CH2:9][CH2:10][C@@:11]4([C:27]([OH:29])=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]43)[C:3]2([CH3:33])[CH3:32])=[O:1])[C:4]1([CH3:17])[CH3:5])=[O:38])[C:34]1[CH:9]=[CH:8][CH:7]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 64971Betulinic Acid

Product 1

HCID 50924548HCID 50924548, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (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-carboxylic acid (1.3 g) in pyridine (10 ml) DMAP (0.57 g) was added followed by the crude reaction mixture (anhydride formation). The reaction mixture was stirred at reflux temperature for about 12 hours. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature, diluted with EtOAc, washed with dil HCl, water, followed by brine and dried over Na2SO4, and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography using hexane and ethyl acetate mixtures as an eluent to afford the title compound (300 mg, 15% yield). 1H NMR (300 MHz, CDCl3): δ 7.37-7.33 (5H, m), 5.16 (2H, m), 4.73 (1H, s), 4.61 (1H, s), 4.45-4.36 (1H, m), 3.65-3.6 (1H, m), 3.1-2.90 (1H, m), 2.85-2.6 (3H, m), 2.4 (1H, m), 2.3-1.9 (5H, m), 1.8-1.3 (17H, m), 1.26 (4H, m), 1.24 (3H, s), 1.22 (2H, m), 1.16 (3H, s), 1.14 (3H, s), 1.00 (2H, m), 0.8 (6H, s); Mass: [M+Na]+ 723 (15%); IR (KBr, cm−1): 3427, 2953, 17330, 1730, 1459, 1376, 1277, 1236, 1187, 1107, 1034, 940, 882.

Workup

  1. temperatureat reflux temperature for about 12 hours
  2. customAfter completion of the reaction (monitored by TLC)
  3. washwashed with dil HCl, water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude reaction mixture
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f58c5cb2645248a9858b8d17ca1c7045
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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