Lauric Acid → benzyl N-lauroyl-L-alanyl-D-isoglutaminate

HRID 2073171Notes

Reaction equation

HRID 2073171 reaction equation
ClC(OCC(C)C)=O.[C:9]([OH:22])(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl.[NH2:24][C@H:25]([C:27]([NH:29][C@@H:30]([C:43](=[O:45])[NH2:44])[CH2:31][CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:28])[CH3:26].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(N(CC)CC)C.O>[C:9]([NH:24][C@H:25]([C:27]([NH:29][C@@H:30]([C:43](=[O:45])[NH2:44])[CH2:31][CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])=[O:28])[CH3:26])(=[O:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 3893Lauric AcidHCID 8857Ethyl AcetateHCID 62365Isobutyl chloroformateHCID 12873810benzyl L-alanyl-D-isoglutaminate hydrochloride

Product 1

HCID 12883973benzyl N-lauroyl-L-alanyl-D-isoglutaminateYield 15.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
0 °C

Procedure

Isobutyl chloroformate (2.54 cc) is added to a solution, kept at 0° C., of lauric acid (3.9 g) in anhydrous toluene (156 cc) and triethylamine (2.7 cc). The mixture is stirred for 20 minutes at 0° C. and a solution, cooled to 0° C., of benzyl L-alanyl-D-isoglutaminate hydrochloride (6.7 g) in water (52 cc) and triethylamine (2.7 cc) is then added. The reaction mixture is stirred for 65 hours at a temperature of the order of 20° C. to yield a reaction mixture of gelatinous appearance, to which ethyl acetate (150 cc) is added. The precipitate is filtered off, washed with water (30 cc) and then dried to yield: benzyl N-lauroyl-L-alanyl-D-isoglutaminate (7.6 g) in the form of a white powder. The aqueous phase of the above filtrate is extracted twice with ethyl acetate (100 cc in total), the ethyl acetate phase is combined with the organic phase of the filtrate and the combined phase is washed with 0.1N hydrochloric acid (125 cc) and water (120 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (20 mm Hg) at 50° C. to yield a further 1.5 g of benzyl N-lauroyl-L-alanyl-D-isoglutaminate. The product (7.6 g and 1.5 g) is recrystallised from methanol (120 cc) to yield benzyl N-lauroyl-L-alanyl-D-isoglutaminate (6.6 g) which melts at 169° C.

Workup

  1. additionis then added
  2. stirringThe reaction mixture is stirred for 65 hours at a temperature of the order of 20° C.
  3. customto yield
  4. additiona reaction mixture of gelatinous appearance
  5. filtrationThe precipitate is filtered off
  6. washwashed with water (30 cc)
  7. customdried to yield
  8. extractionThe aqueous phase of the above filtrate is extracted twice with ethyl acetate (100 cc in total)
  9. washthe combined phase is washed with 0.1N hydrochloric acid (125 cc) and water (120 cc)
  10. dry with materialdried over magnesium sulphate
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg) at 50° C.

Sources & evidence

ORD record
ord-56a28d67f84641dd9b33a16b6fa4676c
Source dataset
uspto-grants-1990_04
Patent number
US04916119

Reaction notes

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