Water → HCID 22418598, compound

HRID 1720807Notes

Reaction equation

HRID 1720807 reaction equation
[C:1]([O:18][CH:19]([CH2:27][O:28][C:29](=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:20][S:21][CH2:22][CH2:23][C:24]([OH:26])=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].Cl.[C:47]([O:51][C:52](=[O:55])[CH2:53][NH2:54])([CH3:50])([CH3:49])[CH3:48].O>CN(C)C=O.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>[C:47]([O:51][C:52](=[O:55])[CH2:53][NH:54][C:24](=[O:26])[CH2:23][CH2:22][S:21][CH2:20][CH:19]([O:18][C:1](=[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])[CH2:27][O:28][C:29](=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH3:50])([CH3:49])[CH3:48]

Participants

7

Reactant 3

HCID 962WaterHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acid

Product 1

HCID 22418598HCID 22418598, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 76257Diethyl cyanophosphonateSolvent

Procedure

To a solution of 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (200 mg) and glycine t-butyl ester hydrochloride (60 mg) in dimethylformamide (3 ml), triethylamine (0.099 ml) and diethyl cyanophosphate (72 ml) were added, followed by stirring at room temperature for 17 hours. After addition of water, the reaction mixture was extracted with chloroform. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium. hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3) to yield the title compound (206 mg, yield 90%) as a wax-like substance.

Workup

  1. additionwere added
  2. extractionthe reaction mixture was extracted with chloroform
  3. washThe extract was washed with a 5% aqueous solution of citric acid
  4. dry with materialhydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-fbc882bfba8f48ba8f27733d9a6cfb08
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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