11-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione → (4S)-11-{2-[(4,5-dihydro-thiazol-2-ylsulfanylmethyl)-dimethylsilanyl]-ethyl}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246548Notes

Reaction equation

HRID 2246548 reaction equation
I[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.[SH:34][C:35]1[S:36][CH2:37][CH2:38][N:39]=1>>[S:36]1[CH2:37][CH2:38][N:39]=[C:35]1[S:34][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

Participants

3

Reactant 2

HCID 5765938311-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dioneHCID 178527880HCID 178527880, compound

Product 1

HCID 25261730(4S)-11-{2-[(4,5-dihydro-thiazol-2-ylsulfanylmethyl)-dimethylsilanyl]-ethyl}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Procedure

Prepared according to Procedure F using Compound 4 and 2-mercaptothiazoline, the crude product was purified on a silica gel column using 3% ethanol in dichloromethane to obtain the pure product in 65% yields.

Workup

  1. customPrepared
  2. customthe crude product was purified on a silica gel column
  3. customto obtain the pure product in 65%
  4. customyields

Sources & evidence

ORD record
ord-1f73a4ffbf624f98ac27e726259f30e3
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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