Ethyl Acetate → HCID 71269701, compound

HRID 401845Notes

Reaction equation

HRID 401845 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7][C:8]([CH3:21])([CH3:20])[C:9]#[C:10][C:11]1[S:15][CH:14]=[C:13]([NH:16][CH:17]([CH3:19])[CH3:18])[CH:12]=1.CCN([CH:28]([CH3:30])[CH3:29])C(C)C.CC[O:33][C:34](C)=[O:35]>CN(C=O)C.ClCCCl>[CH3:7][C:8]([CH3:20])([CH3:21])[C:9]#[C:10][C:11]1[S:15][C:14]([C:34]([OH:33])=[O:35])=[C:13]([N:16]([CH:17]([CH3:18])[CH3:19])[C:1]([C@H:2]2[CH2:10][CH2:9][C@H:8]([CH3:7])[CH2:30][C@@H:28]2[CH3:29])=[O:5])[CH:12]=1

Participants

7

Reactant 4

HCID 8857Ethyl Acetate2×HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 71230626HCID 71230626, compound

Product 1

HCID 71269701HCID 71269701, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of carboxylic acid (200 mg, 1.3 mmol) and DMF (1 drop) in EtOAc (5 mL) was added oxalyl chloride (0.3 mL, 3.45 mmol) at room temperature. The reaction was stirred for 2 h and the volatiles were removed in vacuo. A solution of 5-(3,3-dimethylbut-1-ynyl)-N-isopropylthiophen-3-amine (170 mg, 0.77 mmol) and DIEA (0.3 mL) in DCE (1 mL) was then added. The reaction was stirred overnight. The mixture was poured into EtOAc (150 mL), and the organics were washed with saturated NaHCO3 (2×50 mL) and brine (50 mL). After drying over Na2SO4, the organic layer was concentrated and the residue purified by silica gel chromatography (0-20% EtOAc in hexanes) to give the desired product (116 mg, 25% yield) as a dark oil.

Workup

  1. customthe volatiles were removed in vacuo
  2. stirringThe reaction was stirred overnight
  3. washthe organics were washed with saturated NaHCO3 (2×50 mL) and brine (50 mL)
  4. dry with materialAfter drying over Na2SO4
  5. concentrationthe organic layer was concentrated
  6. customthe residue purified by silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-339e1eb011a14b06a1c84003bbb0e6ce
Source dataset
uspto-grants-2014_06
Patent number
US08741946B2

Reaction notes

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