2-Mercaptoethanol → (4S)-4-ethyl-4-hydroxy-11-{2-[(2-hydroxy-ethylsulfanylmethyl)-dimethyl-silanyl]-ethyl}-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246549Notes

Reaction equation

HRID 2246549 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][CH2:35][CH2:36][OH:37]>>[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][S:34][CH2:35][CH2:36][OH:37])([CH3:32])[CH3:33])=[C:7]2[CH:31]=[CH:30][CH:29]=[CH:28][C:8]2=[N:9][C:10]3=1)[CH3:26]

Participants

3

Reactant 2

HCID 15672-MercaptoethanolHCID 5765938311-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Product 1

HCID 25261567(4S)-4-ethyl-4-hydroxy-11-{2-[(2-hydroxy-ethylsulfanylmethyl)-dimethyl-silanyl]-ethyl}-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-mercaptoethanol, the crude product was purified on a silica gel column using 3% ethanol in dichloromethane to obtain the pure product in 83% yields.

Workup

  1. customPrepared
  2. customthe crude product was purified on a silica gel column
  3. customto obtain the pure product in 83%
  4. customyields

Sources & evidence

ORD record
ord-1e88e6c4097d4fbca29f36b2f1922b8c
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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