Methanol → HCID 178435469, compound

HRID 1872013Notes

Reaction equation

HRID 1872013 reaction equation
[C:1]([CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:45])[CH2:11][NH:12][C:13]2[N:18]=[C:17]([N:19]3[CH:24]=[C:23]([CH:25]4[C:31]5[CH:32]=[CH:33][C:34]([CH2:36][CH3:37])=[CH:35][C:30]=5[CH:29]=[CH:28][C:27]5[CH:38]=[C:39]([CH3:42])[CH:40]=[CH:41][C:26]4=5)[C:22](=[O:43])[NH:21][C:20]3=[O:44])[CH:16]=[CH:15][N:14]=2)[S:7][CH:8]=1)#[N:2].C[Sn]([N:50]=[N+:51]=[N-:52])(C)C.CO>C1(C)C=CC=CC=1>[CH2:36]([C:34]1[CH:33]=[CH:32][C:31]2[CH:25]([C:23]3[C:22](=[O:43])[NH:21][C:20](=[O:44])[N:19]([C:17]4[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH2:11][C:10]([NH:9][C:6]5[S:7][CH:8]=[C:4]([CH2:3][C:1]6[NH:52][N:51]=[N:50][N:2]=6)[N:5]=5)=[O:45])[N:18]=4)[CH:24]=3)[C:26]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][C:27]=3[CH:28]=[CH:29][C:30]=2[CH:35]=1)[CH3:37]

Participants

5

Reactant 3

HCID 887MethanolHCID 5104973Azido(trimethyl)stannaneHCID 18689746HCID 18689746, compound

Product 1

HCID 178435469HCID 178435469, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the product of step (iv) (0.35 g) and trimethyltin azide (0.5 g) in toluene (10 ml) was heated at reflux for 48 hours. Methanol was added and the resultant precipitate filtered off. The solution was evaporated to dryness and the residue purified by reverse phase chromatography. The fraction containing product was concentrated under reduced pressure, acidified with 2N HCl and extracted with ethyl acetate. The extract was evaporated to dryness and the residue triturated with diethyl ether. The product was collected by filtration. Yield 0.16 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. filtrationthe resultant precipitate filtered off
  4. customThe solution was evaporated to dryness
  5. customthe residue purified by reverse phase chromatography
  6. additionThe fraction containing product
  7. concentrationwas concentrated under reduced pressure
  8. extractionextracted with ethyl acetate
  9. customThe extract was evaporated to dryness
  10. customthe residue triturated with diethyl ether
  11. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-8f14c8325ada447b80e8569b2c243890
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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