Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → rel-(3AR,4R,5R,6aS)-4-((R,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

HRID 584877Notes

Reaction equation

HRID 584877 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]1([C:24]2[CH:59]=[CH:58][C:27]([C:28]([O:30][C@@H:31]3[CH2:39][C@@H:34]4[O:35][C:36](=[O:38])[CH2:37][C@@H:33]4[C@H:32]3/[CH:40]=[CH:41]/[C@@H:42]([O:51]C3CCCCO3)[CH2:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:29])=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[OH:51][C@H:42]([CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)/[CH:41]=[CH:40]/[C@@H:32]1[C@@H:33]2[C@@H:34]([O:35][C:36](=[O:38])[CH2:37]2)[CH2:39][C@H:31]1[O:30][C:28](=[O:29])[C:27]1[CH:58]=[CH:59][C:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10188059(3aR,4R,5R,6aS)-Hexahydro-5-(p-phenylbenzoyloxy)-4-[(3S)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1E-pentenyl]-2H-cyclopenta[b]furan-2-one

Product 1

HCID 9982721rel-(3AR,4R,5R,6aS)-4-((R,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

Pyridinium p-toluenesulfonate (20 mg) was added to a stirred solution of the compound [8a] (0.44 g), obtained in previous step, in methanol (20 mL) at room temperature. The mixture was stirred at 40-50° C. for 3-4 hours (TLC monitoring) and evaporated under reduced pressure. The residue was diluted with dichloromethane (30 mL). The solution was washed with saturated aqueous solution of sodium bicarbonate (10 mL) and brine(10 mL), dried over sodium sulfate, filtered and evaporated to give 0.35 g (93.4%) of oily residue. The residue was crystallized from a mixture of hexane and ether to give compound [6a] as white crystals with mp 81-83° C. and [α]D20 −124.5° (c 1, MeCN). 1H NMR (CDCl3) δ: 7.08-8.05 (m, 14H); 5.51-5.74 (m, 2H); 5.21-5.30 (m, 1H); 5.02-5.07 (m, 1H); 4.09-4.13 (m, 1H); 2.46-2.92 (m, 7H); 2.18-2.28 (m, 1H); 1.66-1.86 (m, 3H). 13C (CDCl3) δ: 31.6; 34.8; 37.6; 38.7; 42.7; 54.1; 71.6; 79.0; 83.1; 125.9; 127.1; 127.2; 128.2; 128.3; 128.8; 128.9; 130.1; 136.2; 139.9; 141.5; 146.1; 165.9; 176.2.

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue was diluted with dichloromethane (30 mL)
  3. washThe solution was washed with saturated aqueous solution of sodium bicarbonate (10 mL) and brine(10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0166745728584466aa72418ad4257ce1
Source dataset
uspto-grants-2005_08
Patent number
US06927300B2

Reaction notes

Loading…