Benzyl-5-(N-FMOC-L-valyloxy)-4-stearoyloxy-2-pentenoate → 5-(N-FMOC-L-valyloxy)-4-stearoyloxy-pentanoic Acid

HRID 489066Notes

Reaction equation

HRID 489066 reaction equation
[C:1]([NH:18][C@H:19]([C:23]([O:25][CH2:26][CH:27]([O:40][C:41](=[O:59])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:28]=[CH:29][C:30]([O:32]CC1C=CC=CC=1)=[O:31])=[O:24])[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]>C(OCC)(=O)C.[Pd]>[C:1]([NH:18][C@H:19]([C:23]([O:25][CH2:26][CH:27]([O:40][C:41](=[O:59])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:24])[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

4

Reactant 1

HCID 53974693Benzyl-5-(N-FMOC-L-valyloxy)-4-stearoyloxy-2-pentenoate

Product 1

HCID 233875575-(N-FMOC-L-valyloxy)-4-stearoyloxy-pentanoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 5-(N-FMOC-L-valyloxy)-4-stearoyloxy-2-pentenoate (3.8 g, 4.69 mmole) in 50 ml ethyl acetate was hydrogenated with 10% palladium on charcoal (0.5 g) at normal pressure for five hours at room temperature. The catalyst was filtered and washed with ethyl acetate and 1,4-dioxane. The solution was evaporated under reduced pressure Yield: 3.3 g=99%

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethyl acetate and 1,4-dioxane
  3. customThe solution was evaporated under reduced pressure Yield: 3.3 g=99%

Sources & evidence

ORD record
ord-07b899b134dc41ebbebec3274db0265f
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

Loading…