HCID 19388973, compound → HCID 19389037, compound

HRID 1757791Notes

Reaction equation

HRID 1757791 reaction equation
C1(C[O:8][C:9](=[O:63])[CH2:10][N:11]([C:23]2[CH:28]=[C:27]([C:29]([O: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][CH2:44][CH3:45])=[O:30])[CH:26]=[C:25]([C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[O:47])[CH:24]=2)[CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])C=CC=CC=1>[Pd].C(OCC)(=O)C.C1COCC1>[C:9]([CH2:10][N:11]([C:23]1[CH:28]=[C:27]([C:29]([O: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][CH2:44][CH3:45])=[O:30])[CH:26]=[C:25]([C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[O:47])[CH:24]=1)[CH2:12][C:13]([OH:15])=[O:14])([OH:63])=[O:8]

Participants

5

Reactant 1

HCID 19388973HCID 19388973, compound

Product 1

HCID 19389037HCID 19389037, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.43 g of N-[3,5-bis[(tetradecyloxy)carbonyl]phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester and 0.2 g of 10% palladium on carbon in 30 ml of ethyl acetate and 20 ml of THF was shaken under an initial hydrogen pressure of 51 psi for 2 hours. The catalyst was removed by filtration andthe filtrate was concentrated at reduced pressure to a solid which was recrystallized from methanol-water to give 0.28 g (82% yield, mp 84°-87°) of N-(carboxy-methyl)-N-[3,5-bis[(tetradecyloxy)carbonyl]phenyl]glycine.

Workup

  1. customThe catalyst was removed by filtration andthe filtrate
  2. concentrationwas concentrated at reduced pressure to a solid which
  3. customwas recrystallized from methanol-water

Sources & evidence

ORD record
ord-0f4295c10d3a49da8700e214b956b54d
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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