Decanoyl chloride → n-decylglycine

HRID 1059270Notes

Reaction equation

HRID 1059270 reaction equation
[C:1](Cl)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl.C[O:15][C:16](=[O:19])[CH2:17][NH2:18].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([NH:18][CH2:17][C:16]([OH:19])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 66982Decanoyl chlorideHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 230083n-decylglycine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of decanoyl chloride (5) (2.7 mL, 13 mmol, 1.0 eq) in methylene chloride (20 mL) in an ice/acetone bath was added a mixture of glycine methyl ester hydrochloride (91) (2.0 g, 16 mmol, 1.2 eq) and DIPEA (5.1 mL, 29 mmol, 2.2 eq) in methylene chloride (20 mL) dropwise. The reaction was stirred a further 60 min after complete addition, then washed with 3N hydrochloric acid (50 mL) twice, followed by saturated sodium bicarbonate (50 mL). The organics were dried over magnesium sulfate and the solvents removed under reduced pressure. n-Decylglycine, a compound of formula (96) (3.0 g, 12 mmol, 95%) was obtained, and used in the next step without further purification.

Workup

  1. additionafter complete addition
  2. washwashed with 3N hydrochloric acid (50 mL) twice
  3. dry with materialThe organics were dried over magnesium sulfate
  4. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-2d9d4eeab33047f08d66ca98b2832167
Source dataset
uspto-grants-2003_02
Patent number
US06518242B1

Reaction notes

Loading…