3-(Octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenylcarbamic acid phenylmethyl ester → 5-[3-Amino-5-(octadecyloxy)phenoxy]pentanoic acid methyl ester

HRID 1110253Notes

Reaction equation

HRID 1110253 reaction equation
C1(COC(=O)[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:14]=[C:13]([O: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][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:12]=2)C=CC=CC=1.[H][H]>[Pd].C1COCC1>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:15]1[CH:14]=[C:13]([O: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][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:12]=[C:11]([NH2:10])[CH:16]=1

Participants

5

Reactant 2

HCID 537486613-(Octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenylcarbamic acid phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 543104535-[3-Amino-5-(octadecyloxy)phenoxy]pentanoic acid methyl esterYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.9 g of 3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenylcarbamic acid phenylmethyl ester and 1.5 g of 10% palladium on carbon in 250 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 triturated with hexane and filtered to give 6.8 g (97% yield, mp 57°-59°) of 5-[3-amino-5(octadecyloxy)phenoxy]pentanoic acid methyl ester.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  3. customwas triturated with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b060b4c711044422abb0b27f31fc832f
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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