benzyl-2-(N-FMOC-L-valyloxy)stearate → 2-(N-FMOC-L-valyloxy)stearic acid

HRID 990003Notes

Reaction equation

HRID 990003 reaction equation
C([O:8][C:9](=[O:52])[CH:10]([O:27][C:28](=[O:51])[C@H:29]([CH:48]([CH3:50])[CH3:49])[NH:30][C:31]([O:33][CH2:34][CH:35]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]2[C:36]1=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:32])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:31]([NH:30][C@H:29]([C:28]([O:27][CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9]([OH:52])=[O:8])=[O:51])[CH:48]([CH3:49])[CH3:50])([O:33][CH2:34][CH:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:42]2[C:47]1=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:32]

Participants

4

Reactant 1

HCID 23387558benzyl-2-(N-FMOC-L-valyloxy)stearate

Product 1

HCID 233875212-(N-FMOC-L-valyloxy)stearic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl-2-(N-FMOC-L-valyloxy)stearate (4.4 g, 6.2 mmole) in 50 ml ethyl acetate was hydrogenated with 10% palladium on charcoal (0.5 g) with normal pressure for two hours. The catalyst was filtered and washed with ethyl acetate and 1,4-dioxane. The solution was evaporated under reduced pressure and the product was isolated by silica gel column chromatography. Yield: 3.4 g

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethyl acetate and 1,4-dioxane
  3. customThe solution was evaporated under reduced pressure
  4. customthe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-4a995d05ac6341368ba946393efa52b6
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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