HCID 69320527, compound → HCID 69321446, compound

HRID 1393382Notes

Reaction equation

HRID 1393382 reaction equation
C[O:2][C:3](=[O:34])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=O)[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>CO.[H][H].[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[C:9]([O:8][C:6]([NH:5][C@H:4]([C:3]([OH:34])=[O:2])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[CH:15]=1)=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 1

HCID 69320527HCID 69320527, compound

Product 1

HCID 69321446HCID 69321446, compoundYield 35.7%

Reagents, catalysts & solvents 3

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Palladium hydroxide carbon (50% water content, 180 mg) was added to a solution of N-t-butoxycarbonyl-3-[(2-naphthoyl)methoxy]-L-phenylalanine methyl ester (400 mg, 0.863 mmol) in methanol (13 ml) and the mixture was stirred in hydrogen stream at room temperature for 20 hrs. The catalyst was filtered off and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7) to give N-t-butoxycarbonyl-3-[2-[2-(5,6,7,8-tetrahydro-naphthyl)]ethoxy]-L-phenylalanine methyl ester (132 mg, 34%) and methyl ester of N-t-butoxycarbonyl-3-[2-(2-naphthyl)ethoxy]-L-phenylalanine (134 mg, 34%) (in turn of elution).

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent of the filtrate was distilled off under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7)

Sources & evidence

ORD record
ord-b92df02170a44ae18a270e03b376ee7f
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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