HCID 58100080, compound → HCID 58100137, compound

HRID 1696854Notes

Reaction equation

HRID 1696854 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:45][C@@H:46]([C:48]2[CH:53]=[CH:52][C:51]([O:54]CC3C=CC=CC=3)=[C:50]([CH2:62][OH:63])[CH:49]=2)[OH:47])[CH2:26][C@H:27]([OH:44])[C:28]2[CH:33]=[CH:32][C:31]([O:34]CC3C=CC=CC=3)=[C:30]([CH2:42][OH:43])[CH:29]=2)=[CH:17][CH:16]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:54][C:51]1[CH:52]=[CH:53][C:48]([C@@H:46]([OH:47])[CH2:45][N:25]([CH2:26][C@H:27]([OH:44])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:42][OH:43])[CH:29]=2)[CH2:24][CH2:23][CH2:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:20][CH:19]=2)=[CH:49][C:50]=1[CH2:62][OH:63]

Participants

4

Reactant 1

HCID 58100080HCID 58100080, compound

Product 1

HCID 58100137HCID 58100137, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension containing 65 (250 mg, 0.28 mmol) and palladium catalyst (10% Pd on carbon, 50% wet, 100 mg, 0.94 mmol) in ethanol (10 mL) was bubbled with nitrogen for 20 min. The reaction mixture was vacuumed, then charged with H2 gas (1 atm), and allowed to stir at room temperature for 24 h. The suspension was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol and dichloromethane to afford the desired product 66 (45 mg, 28%) as an off white solid: m/z (ESI) 553 [C32H44N2O6+H]+.

Workup

  1. customwas bubbled with nitrogen for 20 min
  2. additioncharged with H2 gas (1 atm)
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol and dichloromethane

Sources & evidence

ORD record
ord-239b49259cb84959b02776c76b0c57ac
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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