HCID 57242692, compound → HCID 18703968, compound

HRID 2288104Notes

Reaction equation

HRID 2288104 reaction equation
C1(C([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:54]([OH:55])[CH:41]6[CH:42]([C:43]([O:45][NH:46][CH2:47][C:48]7[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=7)=[O:44])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:56]([CH3:58])[CH3:57])=[O:16])C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH2:47]([NH:46][O:45][C:43]([CH:42]1[CH:37]2[CH:38]3[O:39][C:35]([O:34][CH2:33][C:21]45[CH:20]6[CH2:29][C:28]([CH:30]=[O:31])([C:17]4([C:15]([OH:16])=[O:14])[C:18]([CH:56]([CH3:58])[CH3:57])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:54]([OH:55])[CH:41]1[O:40]3)[O:36]2)=[O:44])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

4

Reactant 1

HCID 57242692HCID 57242692, compound

Product 1

HCID 18703968HCID 18703968, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

27 mg of compound (78) was dissolved in 2 ml of ethyl acetate and allowed to react in the presence of a catalytic amount of 10% palladium-carbon under stirring under a hydrogen atmosphere at room temperature for 3 hours. The reaction solution was filtered, and the filtrate was concentrated in vacuo. The reaction product was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm) and eluted with chloroform-methanol (20:1). The fraction containing the desired product was concentrated to dryness to give 18.4 mg of compound (79).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe reaction product was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm)
  4. washeluted with chloroform-methanol (20:1)
  5. additionThe fraction containing the desired product
  6. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-1b1a351c212947cb8e833345b7c50ada
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

Loading…