Methanol → Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, methyl ester, (alphaR,betaS)-

HRID 376233Notes

Reaction equation

HRID 376233 reaction equation
[N:1]([C@@H:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:5]([O:10]CC1C=CC=CC=1)[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-].[CH3:24][OH:25]>[Pd]>[CH3:9][O:8][C:6](=[O:7])[C@H:5]([OH:10])[C@H:4]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:1][C:24](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 18397106HCID 18397106, compound

Product 1

HCID 182104Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, methyl ester, (alphaR,betaS)-Yield 74%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The azide 10 (10 g, 24 mmol) was hydrogenated with 10% Pd/C (2.5 g) in methanol under H2 (50 p.s.i.) for 4 h. The solution was filtered, stood at 23° C. for 48 h, and concentrated. The solid was recrystallized over chloroform-methanol (50:1) to give 16 (5.5 g, 74%):[a]D20=-49 (c 1, CH3OH), lit. [a]D20=-49.6° (c 1, CH3OH); 1H NMR (CD3OD) d 3.68 (s, 3H), 4.60 (d, J=3.8 Hz, 1 H), 5.58 (d, J 3.8 Hz, 1 H), 7.32-7.61 (m, 8 H), 7.98-8.11 (m, 2 H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. customThe solid was recrystallized over chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-33039104fa9641fdaad98a0e74e6e6be
Source dataset
uspto-grants-2000_02
Patent number
US06020174

Reaction notes

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