28-O-benzyldihydrobetulinic acid → HCID 67776761, compound

HRID 2405502Notes

Reaction equation

HRID 2405502 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([CH3:38])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:37])[CH2:9][CH2:10][C@@:11]3([C:27]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])[CH2:23][CH2:22][C@@H:21]([CH:24]([CH3:26])[CH3:25])[C@@H:12]32)[C:3]1([CH3:40])[CH3:39].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:24]([C@H:21]1[C@@H:12]2[C@@H:13]3[C@@:8]([CH3:37])([CH2:9][CH2:10][C@@:11]2([C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28])[CH2:23][CH2:22]1)[C@@:7]1([CH3:38])[C@@H:16]([C@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6]1)[C:3]([CH3:39])([CH3:40])[C:2](=[O:1])[CH2:19][CH2:18]2)[CH2:15][CH2:14]3)([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 46740128-O-benzyldihydrobetulinic acidHCID 178418287HCID 178418287, compound

Product 1

HCID 67776761HCID 67776761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-benzyl 9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (3.3 g, 6.01 mmol) in DCM (50 mL) was added PCC (3.89 g, 18.04 mmol). The reaction mixture was stirred for 4 hours. TLC indicated sm was consumed and desired product was formed. The reaction mixture was concentrated under reduced pressure. The residue was purified by biotage with 0-10% ethyl acetate/hexane to provide the title compound as white solid (3.05, 93%). LCMS: m/e 547.25 (M+H)+, 2.77 min (method 1). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.41-7.28 (m, 5H), 5.10 (q, J=12.41 Hz, 2H), 2.57-2.34 (m, 2H), 2.31-2.16 (m, 3H), 1.98-1.86 (m, 1H), 1.85-1.73 (m, 2H), 1.73-1.61 (m, 1H), 1.54-1.07 (m, 17H), 1.06 (s, 3H), 1.01 (s, 3H), 0.92 (s, 3H), 0.90 (s, 3H), 0.84 (d, J=7.02 Hz, 3H), 0.76 (s, 3H), 0.73 (d, 3H).

Workup

  1. customwas consumed

Sources & evidence

ORD record
ord-f1c4287163344db59889293ec46a4d79
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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