Water → 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoic acid

HRID 1872809Notes

Reaction equation

HRID 1872809 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19][CH:20]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:21][C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19][CH:20]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:21][C:22]([OH:24])=[O:23])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 21970290benzyl 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoate

Product 1

HCID 219702703-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoic acidYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoate (2.85 g) in methanol (50 ml) was added 10% palladium on active carbon (0.5 g) and water (5 ml). The mixture was stirred at room temperature under hydrogen atmosphere for 1 hour. The catalyst was filtered off and the solvent was removed under reduced pressure to give 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoic acid as an oil (2.31 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f4a12902051443a930d1d999cdac17c
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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