1,4-Cyclohexadiene → HCID 140447360, compound

HRID 2297370Notes

Reaction equation

HRID 2297370 reaction equation
C([C:8]1[C:13]([CH:14]=[C:15]([C:17](=[O:31])[NH:18][CH:19]2[CH:27]([OH:28])[CH:26]([OH:29])[CH:22]3[O:23][CH2:24][O:25][CH:21]3[CH:20]2[OH:30])[CH3:16])=[CH:12][C:11]([O:32][P:33](=[O:36])([OH:35])[OH:34])=[C:10]([O:37][CH:38]2[CH:42]([OH:43])[CH:41]([OH:44])[CH:40](/[C:45](=[N:47]/[O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([Cl:56])[CH:51]=3)/[CH3:46])[O:39]2)[C:9]=1CC1C=CC=CC=1)C1C=CC=CC=1.C1CC=CCC=1>[Pd]>[Cl:56][C:52]1[CH:51]=[C:50]([CH:55]=[CH:54][CH:53]=1)[CH2:49][O:48]/[N:47]=[C:45](/[CH:40]1[O:39][CH:38]([O:37][C:10]2[CH:9]=[CH:8][C:13]([CH:14]=[C:15]([C:17](=[O:31])[NH:18][CH:19]3[CH:27]([OH:28])[CH:26]([OH:29])[CH:22]4[O:23][CH2:24][O:25][CH:21]4[CH:20]3[OH:30])[CH3:16])=[CH:12][C:11]=2[O:32][P:33](=[O:34])([OH:36])[OH:35])[CH:42]([OH:43])[CH:41]1[OH:44])\[CH3:46]

Participants

4

Reactant 2

HCID 123431,4-CyclohexadieneHCID 142654912HCID 142654912, compound

Product 1

HCID 140447360HCID 140447360, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of phosphoric acid dibenzyl-(2-(5-(1-(3-chloro-benzyloxy-E-imino)-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-5-(2-(4,6,7-trihydroxy-hexahydro-benzo(1,3)dioxol-5-ylcarbamoyl)-propenyl)-phenyl) ester (95 mg, 0.105 mmol) and 168 mg of 1,4-cyclohexadiene (2.1 mmol) and 95 mg 10% palladium on carbon was stirred under nitrogen for 20 hours. The reaction mixture was filtered through Celite and evaporated. The residue was chromatographed on reversed phase SiO2 (30% methanol/water) to give 63 mg of the title compound; MS m/e 731 (M+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated
  3. customThe residue was chromatographed on reversed phase SiO2 (30% methanol/water)

Sources & evidence

ORD record
ord-6cc63f2bdf9f46bfa07d8de0d8a1ade0
Source dataset
uspto-grants-2002_12
Patent number
US06492342B1

Reaction notes

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