Hydrochloric Acid → HCID 86650013, compound

HRID 1892510Notes

Reaction equation

HRID 1892510 reaction equation
[Br-].[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:10]=1)(=[O:4])[CH3:3].CC(C)([O-])C.[K+].[O:37]1[CH2:41][CH2:40][O:39][CH:38]1[C:42]1[CH:43]=[C:44]([CH:51]=O)[S:45][C:46]=1[Si:47]([CH3:50])([CH3:49])[CH3:48].Cl>CN(C)C=O.O>[O:37]1[CH2:41][CH2:40][O:39][CH:38]1[C:42]1[CH:43]=[C:44]([CH:51]=[CH:11][C:9]2[N:10]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[S:7][CH:8]=2)[S:45][C:46]=1[Si:47]([CH3:50])([CH3:49])[CH3:48]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 86649976{[2-(Acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromideHCID 86650008HCID 86650008, compound

Product 1

HCID 86650013HCID 86650013, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of {[2-(acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromide (7.970 g, 16.03 mmol) in anhydrous N,N-dimethylformamide (32 ml) was added potassium tert-butoxide (3.687 g, 32.86 mmol) at 0° C., and the mixture was stirred for 1 hr. A solution of 4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophene-2-carbaldehyde (2.740 g, 10.69 mmol) in anhydrous N,N-dimethylformamide (6 ml) was added dropwise, and the mixture was stirred for 1 hr. 1M Hydrochloric acid (17.0 ml) and iced water (170 ml) were added, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6) to give N-(4-{2-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (4.010 g, 10.16 mmol, yield 95.0%) as an off-white solid.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted 3 times with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6)

Sources & evidence

ORD record
ord-21e71166ee9c4d00abe405111a9b796e
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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