HCID 21970279, compound → HCID 21970282, compound

HRID 1872790Notes

Reaction equation

HRID 1872790 reaction equation
C([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:15]([O:17][C@@H:18]([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])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])=[O:10])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[C:15]([O:17][C@@H:18]([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])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 21970279HCID 21970279, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21970282HCID 21970282, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3S)-3-[(2S)-5-benzyloxycarbonyl-2-(tertiarybutoxycarbonylamino)pentanoyl]oxyhexadecanamide (100 mg) in methanol (2 ml) was hydrogenated over 10% palladium on carbon (20 mg) under atmospheric pressure of hydrogen for 3.5 hours at room temperature. Then, the catalyst was filtered off with celite and the filtrate was concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate (0.5 ml) and n-hexane (1 ml) to give (3S)-3-[(2S)-5-carboxy-2-(tertiarybutoxycarbonylamino)-pentanoyl]oxyhexadecanamide (40 mg).

Workup

  1. filtrationThen, the catalyst was filtered off with celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from a mixture of ethyl acetate (0.5 ml) and n-hexane (1 ml)

Sources & evidence

ORD record
ord-6bf631961b9b438c8c5e1e0cbc3dbda2
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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