Hexane → HCID 68510474, compound

HRID 1949159Notes

Reaction equation

HRID 1949159 reaction equation
CCN(CC)CC.[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=1[C:19](=[O:21])[CH3:20].[CH2:22]([O:24][C:25](=[O:30])[CH2:26][C:27](Cl)=[O:28])[CH3:23].CCCCCC>C(Cl)Cl.O>[CH2:22]([O:24][C:25](=[O:30])[CH2:26][C:27]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:12]=[CH:11][C:10]=1[C:19](=[O:21])[CH3:20])=[O:28])[CH3:23]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 685205HCID 685205, compound

Product 1

HCID 68510474HCID 68510474, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

160 μl (1.15 mol) NEt3 were added to a solution of 200 mg (1.0 mmol) 1-(2-amino-4-tert-butylphenyl)ethanone in DCM (20 ml) and the mixture was cooled to 0° C. 170 μl (1.4 mmol) 3-chloro-3-oxopropanoic acid ethyl ester were added at this temperature and the mixture was then stirred for 2 h at RT. Then it was diluted with water and extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 19:1) of the residue yielded 190 mg (0.62 mmol, 60%) 3-(2-acetyl-5-tert-butyl-phenylamino)-3-oxopropanoic acid ethyl ester.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-c753280fefb24c3584260ed2c4cd6a51
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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