Palmitoyl chloride → HCID 14127514, compound

HRID 372969Notes

Reaction equation

HRID 372969 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 dimethylformamide 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-1754b1f1845d4586a103e62b58597ce5
Source dataset
uspto-grants-1992_11
Patent number
US05162311

Reaction notes

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