Toyocamycin → HCID 88053963, compound

HRID 2307215Notes

Reaction equation

HRID 2307215 reaction equation
[CH:1]1[N:9]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]2[OH:18])[C:8]2[C:3](=[C:4]([NH2:19])[N:5]=[CH:6][N:7]=2)[C:2]=1[C:20]#[N:21].[C:22]([Si:26](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])([CH3:24])[CH3:23].[CH3:40][S:41](Cl)(=[O:43])=[O:42]>N1C=CC=CC=1>[NH2:19][C:4]1[C:3]2[C:2]([C:20]#[N:21])=[CH:1][N:9]([C@@H:10]3[O:14][C@H:13]([CH2:15][O:16][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:12]([O:17][S:41]([CH3:40])(=[O:43])=[O:42])[C@H:11]3[O:18][S:41]([CH3:40])(=[O:43])=[O:42])[C:8]=2[N:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 11824ToyocamycinHCID 31297Methanesulfonyl chlorideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 88053963HCID 88053963, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of toyocamicin 43 (5.83 g, 20.0 mmol) in anhydrous pyridine (100 mL) at 0° C. was added tert-butylchlorodiphenylsilane (6.2 mL, 24.0 mmol). The resulting mixture was stirred at room temperature for 18 h and then cooled to 0° C., and methanesulfonyl chloride (3.4 mL, 44.0 mmol) was added. The resulting mixture was stirred at room temperature for 2 h, cooled with ice, quenched by adding water (2 mL), and stirred at room temperature for 30 min. The solvent was evaporated. The residue was dissolved in ethyl acetate, washed with brine three times, dried (Na2SO4) and concentrated. Chromatography on silica (ethyl acetatehexanes 3:2) gave 8.41 g of the titled compound as a colorless solid.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe resulting mixture was stirred at room temperature for 2 h
  3. temperaturecooled with ice
  4. customquenched
  5. additionby adding water (2 mL)
  6. stirringstirred at room temperature for 30 min
  7. customThe solvent was evaporated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washwashed with brine three times
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3b4a779a959644b48bd7906708432ed7
Source dataset
uspto-grants-2004_12
Patent number
US06831069B2

Reaction notes

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