N-[Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysyl]-L-threonine → N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-lysyl]-L-threonine

HRID 236509Notes

Reaction equation

HRID 236509 reaction equation
[C:1]([O:18][CH:19]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:20][C:21]([NH:23][C@H:24]([C:40]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[C@@H:44]([CH3:46])[OH:45])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29]C(OCC1C=CC=CC=1)=O)=[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]>O1CCCC1.[Pd]>[C:1]([O:18][CH:19]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:20][C:21]([NH:23][C@H:24]([C:40]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[C@@H:44]([CH3:46])[OH:45])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])=[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 1

HCID 86741316N-[Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysyl]-L-threonine

Product 1

HCID 53945144N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-lysyl]-L-threonineYield 63.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-[Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysyl]-L-threonine (2.4 g) prepared by the method of Example 40 was dissolved in tetrahydrofuran (30 ml), and palladium black (0.3 g) added thereto. The mixture was subjected to catalytic hydrogenation at atmospheric pressure. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel. Elution with a mixture of chloroform and methanol (50:1) afford powder of N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-lysyl]-L-threonine (1.3 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. washElution
  5. additionwith a mixture of chloroform and methanol (50:1)

Sources & evidence

ORD record
ord-9dbe2c0ad1e249e9ba4aaa7c4e69ccff
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

Loading…