HCID 22949454, compound → HCID 22949457, compound

HRID 1700771Notes

Reaction equation

HRID 1700771 reaction equation
[O:1]=[C:2]1[N:6]([C@@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:22]3[C:23]4[CH:44]=[CH:43][C:42]([O:45]CC5C=CC=CC=5)=[CH:41][C:24]=4[S:25][C:26]=3[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:29][CH:28]=3)=[O:21])=[CH:16][CH:15]=2)[CH2:5][CH2:4][O:3]1>[Pd].C1COCC1.CCO>[O:1]=[C:2]1[N:6]([C@@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([C:22]3[C:23]4[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][C:24]=4[S:25][C:26]=3[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][CH2:39][CH2:40]4)=[CH:29][CH:28]=3)=[O:21])=[CH:18][CH:19]=2)[CH2:5][CH2:4][O:3]1

Participants

4

Reactant 1

HCID 22949454HCID 22949454, compound

Product 1

HCID 22949457HCID 22949457, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A slurry of the (±)-6-benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[trans-2-(2-oxooxazolidin-3-yl)cyclohexyloxy]phenyl ketone (Part C) and an equal weight of 10% Pd/C) in a 1:1 mixture of THF-EtOH was stirred under positive hydrogen pressure (from balloon) for about 19 h. The reaction mixture was filtered through a pad of diatomaceous earth and washed with THF. The filtrate was then concentrated under reduced pressure and the residue was flash chromatographed (silica gel, 10%[10% NH40H in MeOH]/CH2Cl2) to afford the title compound in 62% yield.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washwashed with THF
  3. concentrationThe filtrate was then concentrated under reduced pressure
  4. customchromatographed (silica gel, 10%[10% NH40H in MeOH]/CH2Cl2)

Sources & evidence

ORD record
ord-4066e386e0514e71b26361f8d226178e
Source dataset
uspto-grants-2002_02
Patent number
US06350774B1

Reaction notes

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