Methanol → HCID 89246847, compound

HRID 2191052Notes

Reaction equation

HRID 2191052 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@:13]([CH2:24][OH:25])([N:21]=[N+:22]=[N-:23])[O:12]1.C[Si](Cl)(C)C.[C:31](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32].CO>N1C=CC=CC=1>[N:21]([C@@:13]1([CH2:24][OH:25])[C@H:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C@H:15]2[C@H:11]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[NH:1][C:31](=[O:32])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:12]1)=[N+:22]=[N-:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 57824577HCID 57824577, compound

Product 1

HCID 89246847HCID 89246847, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 36.2 (300 mg, 0.86 mmol) was dissolved in 8.6 mL anhydrous pyridine, and treated with TMSCl (1.09 mL, 8.6 mmol). The mixture was stirred for 1 h, and then treated with BzCl (1.0 mL, 8.6 mmol), stirred for overnight. MeOH was added to the mixture after the reaction was completed. The mixture was stirred for another 5 min and then concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with sat. NaHCO3 twice and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 50% EtOAc in hexane to give compound 36.3 (357 mg, 74% yield).

Workup

  1. stirringstirred for overnight
  2. stirringThe mixture was stirred for another 5 min
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with sat. NaHCO3 twice
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-febc01c9870c4b4998773303a4bbeef6
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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