Hydrochloric Acid → HCID 178443427, compound

HRID 2254361Notes

Reaction equation

HRID 2254361 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:7]([C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:8])#[N:2].C([Sn]([N:47]=[N+:48]=[N-:49])(CCCC)CCCC)CCC.Cl.CO>O1CCCC1>[CH2:24]([O:23][C:22]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:8])=[CH:5][C:4]=1[CH2:3][C:1]1[NH:49][N:48]=[N:47][N:2]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4984872Tributyltin azideHCID 14739661HCID 14739661, compound

Product 1

HCID 178443427HCID 178443427, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.0 g of the product from Example 1 and 2.2 g of tri-n-butylstannylazide in 30 ml of tetrahydrofuran was heated at reflux for 10 days. The reaction was allowed to cool to ambient temperature. A mixture of hydrochloric acid and methanol was added, and after stirring for 30 minutes, the mixture was concentrated in vacuo. The residue was purified by chromatography over silica gel eluting with a 30-75% ethyl acetate in hexane gradient which additionally contained 0.05% acetic acid. The appropriate fractions were cooled and concentrated to provide 592 mg of product. Recrystallization from hexane/ethyl acetate provided 580 mg of the desired title product.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 days
  3. additionwas added
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue was purified by chromatography over silica gel eluting with a 30-75% ethyl acetate in hexane gradient which additionally contained 0.05% acetic acid
  6. temperatureThe appropriate fractions were cooled
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e477aaa27ca643cf9e421697e8d2654f
Source dataset
uspto-grants-1993_08
Patent number
US05235064

Reaction notes

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