Sodium Thiosulfate → HCID 58542329, compound

HRID 1951896Notes

Reaction equation

HRID 1951896 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[N:15]3[C:11]([S:12][C:13]([C:19]([N:21]4[CH2:44][C@H:43]([F:45])[CH2:42][C@H:22]4[C:23]([N:25]4[CH2:32][C:29]5([CH2:31][CH2:30]5)[N:28]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:27][C@@H:26]4[CH2:40][OH:41])=[O:24])=[O:20])=[C:14]3[CH:16]([CH3:18])[CH3:17])=[N:10][C@:9]2([C:47]2[CH:48]=[N:49][C:50]([Cl:53])=[CH:51][CH:52]=2)[CH3:46])=[CH:4][C:3]=1[F:54].C(O)(=[O:57])C.C(O)(=O)C.IC1C=CC=CC=1.CC1(C)N([O])C(C)(C)CCC1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[C:36]([O:35][C:33]([N:28]1[CH2:27][C@H:26]([C:40]([OH:57])=[O:41])[N:25]([C:23](=[O:24])[C@@H:22]2[CH2:42][C@@H:43]([F:45])[CH2:44][N:21]2[C:19]([C:13]2[S:12][C:11]3=[N:10][C@:9]([C:47]4[CH:48]=[N:49][C:50]([Cl:53])=[CH:51][CH:52]=4)([CH3:46])[C@@H:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:54])[CH:4]=4)[N:15]3[C:14]=2[CH:16]([CH3:17])[CH3:18])=[O:20])[CH2:32][C:29]21[CH2:31][CH2:30]2)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 58542408HCID 58542408, compound

Product 1

HCID 58542329HCID 58542329, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The compound (100 mg, 0.12 mmol) obtained in Step 2 above was dissolved in a mixed solvent of acetonitrile (1.5 ml) and water (1.5 ml), iodobenzene diacetate (88 mg, 0.26 mmol) and 2,2,6,6-tetramethylpiperidine 1-oxyl (20 mg, 0.12 mmol) were added and the resulting mixture was stirred at room temperature for 4 hours. Aqueous sodium thiosulfate solution (4 ml) was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel chromatography [chloroform:methanol=40:1→10:1 (v/v)] to give the title compound (58 mg, 59%) as a colorless solid.

Workup

  1. additionwere added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel chromatography [chloroform:methanol=40:1→10:1 (v/v)]

Sources & evidence

ORD record
ord-a0c3020f5ba54f5cb65f7575afe9502c
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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