Hydrochloric Acid → HCID 53775222, compound

HRID 236492Notes

Reaction equation

HRID 236492 reaction equation
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:39][C@H:40]([C:44]([NH:46][C@H:47]([C:53]([OH:55])=[O:54])[CH2:48][CH2:49][C:50]([OH:52])=[O:51])=[O:45])[C@@H:41]([CH3:43])[OH:42].C(N(CC)CC)C.Cl>O1CCCC1.O>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:39][C@H:40]([C:44]([NH:46][C@H:47]([C:53]([OH:55])=[O:54])[CH2:48][CH2:49][C:50]([OH:52])=[O:51])=[O:45])[C@@H:41]([CH3:43])[OH:42])=[O:23])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 7020163Thr-GluHCID 134890283-Hexadecanoyloxyoctadecanoic acid

Product 1

HCID 53775222HCID 53775222, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (1.5 g) in tetrahydrofuran (100 ml) were added a solution of N-(L-threonyl)-L-glutamic acid (0.79 g) and triethylamine (0.88 ml) in water (220 ml). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off to give a residue which was purified by silica gel column chromatography. Elution with chloroform-methanol (20:1) afforded powder of N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-glutamic acid (1.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationEthyl acetate was distilled off
  5. customto give a residue which
  6. customwas purified by silica gel column chromatography
  7. washElution with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-3b585160bfa945db8bdd08d38307da0a
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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