HCID 53760467, compound → HCID 54481759, compound

HRID 1110272Notes

Reaction equation

HRID 1110272 reaction equation
C1(COC(=O)[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:14]=[C:13]([O:36][CH2:37][CH2:38][CH2:39][P:40]([O:45][CH2:46][CH3:47])([O:42][CH2:43][CH3:44])=[O:41])[CH:12]=2)C=CC=CC=1.[H][H]>[Pd].C1COCC1>[CH2:46]([O:45][P:40]([CH2:39][CH2:38][CH2:37][O:36][C:13]1[CH:14]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:16]=[C:11]([NH2:10])[CH:12]=1)(=[O:41])[O:42][CH2:43][CH3:44])[CH3:47]

Participants

5

Reactant 2

HCID 53760467HCID 53760467, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54481759HCID 54481759, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.47 g of [3-[3-(diethoxyphosphinyl)propoxy]-5-(octadecyloxy)phenyl]carbamic acid phenylmethyl ester and 0.4 g of 10% palladium on carbon in 100 ml of THF was stirred in a hydrogen atmosphere at room temperature for 2.5 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from ether-hexane to give 1.83 g (92% yield, mp 63°-65°) of [3-[3-amino-5-(octadecyloxy)phenoxy]propyl]phosphonic acid diethyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  3. customwas recrystallized from ether-hexane

Sources & evidence

ORD record
ord-1b6cb89748744b07a676e70a6c55b9f3
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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