HCID 54174593, compound → HCID 18654575, compound

HRID 2225627Notes

Reaction equation

HRID 2225627 reaction equation
C([O:8][C:9](=[O:28])[C@@H:10]([NH2:27])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13][CH:12]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:27][C@@H:10]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13][CH:12]=1)[C:9]([OH:28])=[O:8]

Participants

5

Reactant 2

HCID 54174593HCID 54174593, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18654575HCID 18654575, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of (S)-alpha-amino-N-[[(1,1 -dimethyethyl)oxy]carbonyl]-4-[[2-(cyclohexyloxy) ethyl]oxy]benzeneacetic acid benzyl ester (2.15 g) in dichloromethane (15 mL) containing trifluoroacetic acid (15 mL) was stirred at room temperature for 1 hour. After the solvents were removed under reduced pressure, the residue was dissolved in ethyl acetate and the mixture was basified to ~pH 9.5 with concentrated ammonium hydroxide. The organic layer was washed in turn with ammonium bicarbonate solution and brine, then was dried over anhydrous potassium carbonate (K2CO3) and evaporated to give 1.3 g of (S)-alpha-amino-4-[[2-(cyclohexyloxy)ethyl]oxy]benzeneacetic acid benzyl ester. A solution of the crude ester (1.25 g) in methanol (50 mL) was hydrogenated over 10% Pd/C at ambient temperature and pressure until the uptake of hydrogen had ceased. The reaction was diluted with methanol (100 ml), heated to reflux for five minutes, then the catalyst was filtered off through a bed of Celite, and washed with hot methanol (3×30 mL). The combined filtrates were concentrated at reflux to ~50 mL, then were cooled and the solids collected by filtration to yield 0.65 g of (S)-alpha-amino-4-[[2(cyclohexyloxy)ethyl]oxy]benzeneacetic acid, mp 219°-220° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for five minutes
  3. filtrationthe catalyst was filtered off through a bed of Celite
  4. washwashed with hot methanol (3×30 mL)
  5. concentrationThe combined filtrates were concentrated
  6. temperatureat reflux to ~50 mL
  7. temperaturewere cooled
  8. filtrationthe solids collected by filtration

Sources & evidence

ORD record
ord-6d4d11e02d4b4cb0b734bca8c1e93566
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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