HCID 70160773, compound → HCID 70159678, compound

HRID 842613Notes

Reaction equation

HRID 842613 reaction equation
Br.[N+:2]([C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[O:7][CH2:8][C:9]([CH2:11][NH:12][C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=O)([O-])=O.[H][H]>C(O)C.[Pt]>[O:7]1[C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]=2[NH:2][CH:9]([CH2:11][NH:12][C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:8]1

Participants

5

Reactant 2

HCID 70160773HCID 70160773, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70159678HCID 70159678, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

The product from Example 1E (9.7 g, 24.5 mmol) and 5% Pt/C (2.0 g) in ethanol (1 L) was hydrogenated for 16 hours at ambient temperature under 4 atm of hydrogen, filtered through Celite® and concentrated to provide a mixture of diastereomers. The diastereomers were separated by flash chromatography on silica gel with 100:1:1 diethyl ether:ethanol:triethylamine to provide the title compound as the more mobile band. Rf 0.38 (100:1:1 diethyl ether:ethanol:triethylamine); mp 91-92° C.; [α]23D −3.4° (c 1.105, CHCl3); 1H NMR (300 MHz, CDCl3) δ1.35 (d, 3H), 1.45 (bs, 1H), 2.50-2.62 (m, 2H), 3.33 (bm, 1H), 3.73 (q, 1H), 3.86 (dd, 1H), 4.15 (dd, 1H), 4.21 (bs, 1H), 6.62 (m, 2H), 6.75 (m, 2H), 7.20-7.40 (m, 5H).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. customto provide
  4. additiona mixture of diastereomers
  5. customThe diastereomers were separated by flash chromatography on silica gel with 100:1:1 diethyl ether

Sources & evidence

ORD record
ord-98e6138978ed4cc79f3fdf6e4d0603f3
Source dataset
uspto-grants-2002_04
Patent number
US06376488B1

Reaction notes

Loading…