Phosphorus trichloride → HCID 54427159, compound

HRID 1720824Notes

Reaction equation

HRID 1720824 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].C(OC(COC(=O)CCCCCCCCCCCCCCC)CSCCC(NCC1C=CC(C(N[C@H](C(O)=O)CCC(O)=O)=O)=CC=1)=O)(=O)CCCCCCCCCCCCCCC.[C:110]([O:114][C:115](=[O:123])[C:116]1[CH:121]=[CH:120][C:119]([NH2:122])=[CH:118][CH:117]=1)([CH3:113])([CH3:112])[CH3:111].P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:110]([O:114][C:115](=[O:123])[C:116]1[CH:117]=[CH:118][C:119]([NH:122][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])=[CH:120][CH:121]=1)([CH3:113])([CH3:111])[CH3:112]

Participants

6

Reactant 4

HCID 24387Phosphorus trichlorideHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 10843463HCID 10843463, compound

Product 1

HCID 54427159HCID 54427159, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (2.0 g), 4-aminobenzoic acid t-butyl ester (600 mg) and phosphorus trichloride (207 mg) in pyridine (40 ml) was stirred at room temperature for 30 minutes. After solvent concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (chloroform) to yield the title compound (2.157 g, yield 99%) as a colorless solid.

Workup

  1. concentrationAfter solvent concentration under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-4d8ebfcb91b14eda814eac9ef3b57675
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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