Boc-N-Me-Phe-OH → N-Boc-N-methyl-3-cyclohexanyl-L-alanine

HRID 746231

Reaction equation

HRID 746231 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[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].[H][H]>O1CCCC1.[Rh]>[C:1]([O:5][C:6]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 7010602Boc-N-Me-Phe-OHHCID 178418361HCID 178418361, compound

Product 1

HCID 66590605N-Boc-N-methyl-3-cyclohexanyl-L-alanineYield 71.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.8 g of t-butoxycarbonyl-N-methylphenylalanine in 150 ml of tetrahydrofuran was hydrogenated at 60° for about four days using 60 psi hydrogen gas and 5% rhodium on carbon. The mixture was filtered and the filtrate concentrated to give the title compound (3.5 g) as a colorless oil. The oil was used without further purification. Structure assignment was supported by the nmr spectrum (loss of aromatic protons and appearance of cyclohexyl protons) and by elemental analysis.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3dcd5c79227146e9b2fa48517e5cdbab
Source dataset
uspto-grants-1986_07
Patent number
US04603121

Linked notes

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