Palmitoyl chloride → HCID 14127514, compound

HRID 1109451Notes

Reaction equation

HRID 1109451 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:8]=[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=[C:11]([CH2:13][P:14]([OH:17])([OH:16])=[O:15])[CH:12]=1)[C:3]([OH:5])=[O:4].[C:24](Cl)(=[O:40])[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][CH2:38][CH3:39]>CN(C)C=O.C(N(C(C)C)C(C)C)C>[C:24]([NH:1][CH:2]([CH2:6][C:7]1[CH:8]=[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=[C:11]([CH2:13][P:14]([OH:17])([OH:16])=[O:15])[CH:12]=1)[C:3]([OH:5])=[O:4])(=[O:40])[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][CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 8206Palmitoyl chlorideHCID 10427052HCID 10427052, compound

Product 1

HCID 14127514HCID 14127514, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a mixture of 335 mg (±)-α-amino-3-(5-phosphonomethyl-[1.1'-biphenyl]3-yl) propanoic acid in 30 ml dimethyl formamide and 0.76 ml N-ethyldiisopropylamine under nitrogen are added dropwise at room temperature within 10 minutes 0.4 ml palmitic acid chloride. The mixture is stirred at room temperature for 26 hours. The solvent is evaporated in vacuo. The oily residue is taken up in water, acidified with 2N HCl to pH 1 and extracted with diethyl ether. The extract is washed with saturated aqueous sodium chloride solution, dried (Na2SO4) and evaporated. The residue is recrystallized from diethyl ether/petroleum ether to yield the title compound, m.p. 130°-140°. MS (FAB):574(MH+).

Workup

  1. customThe solvent is evaporated in vacuo
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue is recrystallized from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-625bd1773bba4de983a04adb4cedcaa0
Source dataset
uspto-grants-1994_06
Patent number
US05321016

Reaction notes

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