Acetic Acid → (2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

HRID 703198Notes

Reaction equation

HRID 703198 reaction equation
[CH3:1][C:2]([CH3:19])([O:4][C:5]([NH:7][C@H:8]([C:16]([OH:18])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].CO.C1(C)C=CC=CC=1.C(O)(=O)C>[Pt]=O.C(O)C>[CH3:3][C:2]([CH3:19])([O:4][C:5]([NH:7][C@@H:8]([CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:16]([OH:18])=[O:17])=[O:6])[CH3:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 1140TolueneHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Platinum oxide catalyst (5 g) is added to a solution of N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine (120 g, 0.452 mole) in absolute ethanol (1 l). The mixture is placed on a Parr reduction apparatus at 50 lb. pressure. The absorption of hydrogen is rapid and the hydrogen reservoir needs continued refilling. The reduction proceeds overnight and after 20 hours is completed. The mixture is filtered through Celite and concentrated in vacuo to give 124.4 g of the title F compound as a glassy solid colorless residue; [α]D =-9.5° (c=1, methanol). TLC (silica gel; toluene:acetic acid, 4:1) Rf =0.62.

Workup

  1. customThe absorption of hydrogen
  2. filtrationThe mixture is filtered through Celite
  3. concentrationconcentrated in vacuo
  4. customto give 124.4 g of the title F compound as a glassy solid colorless residue

Sources & evidence

ORD record
ord-fbcad866dfd940e7b8dd7a8f9fb84bc5
Source dataset
uspto-grants-1991_01
Patent number
US04981843

Reaction notes

Loading…