Glycine → N-Dodecamidoglycine

HRID 252473

Reaction equation

HRID 252473 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C(N(C(C)C)CC)(C)C.[CH2:15]([N:27]=C=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].CN(C=[O:34])C>O.O1CCCC1>[C:15]([NH:27][NH:1][CH2:2][C:3]([OH:5])=[O:4])(=[O:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 750GlycineHCID 6228DimethylformamideHCID 77873Dodecane, 1-isocyanato-HCID 81531Diisopropylethylamine

Product 1

HCID 86599604N-Dodecamidoglycine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Glycine (0.40 g, 5.25 mmol) and 0.91 mL of diisopropylethylamine (5.25 mmol) were dissolved in 4 mL DMF and 6 mL water. Dodecylisocyanate (0.72 mL, 3.0 mmol) in 7 mL tetrahydrofuran was added and the mixture was stirred for 1 h at room temperature. Water (40 mL) was added and the resulting mixture was washed with ethyl acetate twice. The aqueous layer was acidified with 6N HCl, the resulting precipitate was filtered, and then dried to provide 575 mg of the title compound.

Workup

  1. washthe resulting mixture was washed with ethyl acetate twice
  2. filtrationthe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-107a21eddf7c429fa48da28ebabfc9ee
Source dataset
uspto-grants-2011_01
Patent number
US07868135B2

Linked notes

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