Ethyl Acetate → HCID 23449266, compound

HRID 1839334Notes

Reaction equation

HRID 1839334 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][C:14]([C:16]2[N:17]=[CH:18][N:19]3[CH:23]=[CH:22][S:21][C:20]=23)=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:26]([Sn:30](Cl)([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][C:14]([C:16]2[N:17]=[CH:18][N:19]3[CH:23]=[C:22]([Sn:30]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:26][CH2:27][CH2:28][CH3:29])[S:21][C:20]=23)=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 15096Tributyltin ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 23449147HCID 23449147, compound

Product 1

HCID 23449266HCID 23449266, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-70 °C

Procedure

7-(4-Nitrobenzyloxycarbonylamino)acetylimidazo[5,1-b]thiazole (2.52 g) was suspended in 50 ml of anhydrous THF. The suspension, was cooled in an argon atmosphere to −70° C. Tri-n-butylstannyl chloride (3 ml) was added to the suspension. A solution (31.5 ml) of 1 N lithiumbis(trimethylsilyl)amide in THF was then added dropwise thereto over a period of 20 min. The mixture was allowed to react at the same temperature for one hr. The reaction solution was poured into a mixed solution composed of 250 ml of ethyl acetate and 150 ml of 15% brine. The organic layer was washed with 15% brine, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate:dichloromethane=1:10) to give 1.41 g of the title compound.

Workup

  1. customto react at the same temperature for one hr
  2. additionThe reaction solution was poured into a mixed solution
  3. washThe organic layer was washed with 15% brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:dichloromethane=1:10)

Sources & evidence

ORD record
ord-07b1e084100f403eae3bef811f3b356f
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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