Hydrochloric Acid → HCID 90100317, compound

HRID 2207302Notes

Reaction equation

HRID 2207302 reaction equation
C(OC(=O)[N:7]([S:13]([C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:8]1[S:9][CH:10]=[CH:11][N:12]=1)(C)(C)C.C([Li])CCC.[O:29]1[CH:33]=[CH:32][C:31]([C:34]2[N:41]=[CH:40][CH:39]=[CH:38][C:35]=2[CH:36]=[O:37])=[CH:30]1.Cl>O1CCCC1.O.C(OCC)(=O)C>[O:29]1[CH:33]=[CH:32][C:31]([C:34]2[C:35]([CH:36]([OH:37])[C:19]3[CH:18]=[CH:17][C:16]([S:13]([NH:7][C:8]4[S:9][CH:10]=[CH:11][N:12]=4)(=[O:14])=[O:15])=[CH:21][CH:20]=3)=[CH:38][CH:39]=[CH:40][N:41]=2)=[CH:30]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 86672843HCID 86672843, compoundHCID 118522199HCID 118522199, compoundHCID 178418339Butyllithium

Product 1

HCID 90100317HCID 90100317, compoundYield 11.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

100 mg (0.28 mmol) of tert-butyl((4-fluorophenyl)sulfonyl)(thiazol-2-yl)carbamate was dissolved in 5 mL of tetrahydrofuran under nitrogen gas, and cooled to −78° C. After adding 0.26 mL (0.42 mmol) of n-butyllithium (1.6 M in tetrahydrofuran) slowly, the mixture was stirred for 30 minutes as maintaining −78° C. 23 mg (0.13 mmol) of 2-(furan-3-yl)nicotinaldehyde was dissolved in 0.5 mL of tetrahydrofuran, and added to the above reacting solution. As warming from −78° C. to room temperature, the reacting solution was stirred for 24 hours. Ethyl acetate and water/1 N-hydrochloride were added to the reacting solution, and it was stirred. After separating layers, the organic layer only was collected and concentrated under reduced pressure. The obtained residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=1:1) to obtain 6 mg (5.2% yield) of the title compound.

Workup

  1. temperatureas maintaining −78° C
  2. additionadded to the
  3. temperatureAs warming from −78° C. to room temperature
  4. stirringthe reacting solution was stirred for 24 hours
  5. stirringwas stirred
  6. customAfter separating layers
  7. customthe organic layer only was collected
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c0da594b32764e7aa34e8349de3cb206
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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