Potassium Acetate → acetic acid-(4S)-{[2-(4-ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-11-yl)-ethyl]-dimethylsilanyl}-methyl ester

HRID 2246531Notes

Reaction equation

HRID 2246531 reaction equation
Cl[CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12.[C:34]([O-:37])(=[O:36])[CH3:35].[K+]>CN(C)C=O>[CH2:25]([C@:23]1([OH:24])[C:13]2[CH:12]=[C:11]3[N:16]([C:15](=[O:19])[C:14]=2[CH2:20][O:21][C:22]1=[O:27])[CH2:17][C:18]1[C:6]([CH2:5][CH2:4][Si:3]([CH2:2][O:37][C:34](=[O:36])[CH3:35])([CH3:33])[CH3:32])=[C:7]2[CH:31]=[CH:30][CH:29]=[CH:28][C:8]2=[N:9][C:10]3=1)[CH3:26]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 2522749711-(4S)-[2-(chloromethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Product 1

HCID 25260766acetic acid-(4S)-{[2-(4-ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-11-yl)-ethyl]-dimethylsilanyl}-methyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 3 (200 mg) and potassium acetate (200 mg) in dry N,N-dimethylformamide (4 mL) was heated at 80° C. for 16 hours. The reaction mixture was cooled to room temperature and the N,N-dimethylformamide was removed under vacuum with mild heating. The obtained crude material was directly purified on a silica gel column using 1-2% ethanol in dichloromethane to obtain the required product in 72% yield (150 mg).

Workup

  1. customthe N,N-dimethylformamide was removed under vacuum with mild heating
  2. customThe obtained crude material
  3. customwas directly purified on a silica gel column

Sources & evidence

ORD record
ord-c1e0ba87fc1e474990dbd981354feaa6
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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