HCID 53724108, compound → HCID 53775222, compound

HRID 236512Notes

Reaction equation

HRID 236512 reaction equation
[C:1]([O:18][CH:19]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH2:20][C:21]([NH:23][C@H:24]([C:28]([NH:30][C@H:31]([C:44]([O:46]CC1C=CC=CC=1)=[O:45])[CH2:32][CH2:33][C:34]([O:36]CC1C=CC=CC=1)=[O:35])=[O:29])[C@@H:25]([CH3:27])[OH:26])=[O:22])(=[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].[H][H]>[Pd]>[C:1]([O:18][CH:19]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH2:20][C:21]([NH:23][C@H:24]([C:28]([NH:30][C@H:31]([C:44]([OH:46])=[O:45])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:29])[C@@H:25]([CH3:27])[OH:26])=[O:22])(=[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]

Participants

4

Reactant 2

HCID 53724108HCID 53724108, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53775222HCID 53775222, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-glutamate (48 g) in demethylformamide (500 ml) was hydrogenated over palladium black (1 g) at room temperature at 1 atmospheric pressure. After the theoritical amount of hydrogen was adsorbed, dimethylformamide was removed under reduced pressure. The residual crude crystal was recrystallized from ethanol to give N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-glutamic acid (35.5 g).

Workup

  1. customdimethylformamide was removed under reduced pressure
  2. customThe residual crude crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-1d594aedf111415b909f8016607c56e3
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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