Acetoxyacetyl chloride → Acetic acid [cyclohexylmethyl-(2-hydroxyethyl)carbamoyl]-methyl ester

HRID 1497957Notes

Reaction equation

HRID 1497957 reaction equation
[CH:1]1([CH2:7][NH:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>C(Cl)Cl>[CH:1]1([CH2:7][N:8]([CH2:9][CH2:10][OH:11])[C:26]([CH2:25][O:24][C:21](=[O:23])[CH3:22])=[O:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 132882132-[(Cyclohexylmethyl)amino]ethan-1-ol

Product 1

HCID 67152053Acetic acid [cyclohexylmethyl-(2-hydroxyethyl)carbamoyl]-methyl esterYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(cyclohexylmethylamino)-ethanol (600 mg, 3.8 mmol) in DCM (6 mL) at 0° C. was added DIPEA (588 mg, 4.6 mmol) and then acetoxyacetyl chloride (467 mg, 3.44 mmol) over 5 min. The resulting mixture was warmed to room temperature, stirred overnight under an atmosphere of nitrogen, diluted with DCM and washed successively with 1 N aqueous HCl, saturated NaHCO3, and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield the title compound (914 mg). (m/z): [M+H]+ calcd for C13H23NO4, 258.16. found, 258.0.

Workup

  1. washwashed successively with 1 N aqueous HCl, saturated NaHCO3, and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53fc14b941d94d9a9b05a5e4da971c87
Source dataset
uspto-grants-2015_12
Patent number
US09199993B2

Reaction notes

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