Triethylamine → (3S,4S)-4-(1-t-butyldimethylsilyloxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

HRID 1461606Notes

Reaction equation

HRID 1461606 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C@H:12]1[N:15]([CH:16]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14](=[O:35])[C@@H:13]1[C@H:36]([O:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[CH3:37])=[CH2:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C>C(OCC)(=O)C.[Pt](=O)=O>[Si:1]([O:8][CH2:9][CH:10]([C@@H:12]1[N:15]([CH:16]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14](=[O:35])[C@@H:13]1[C@H:36]([O:38][C:39]([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40])[CH3:37])[CH3:11])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67797177HCID 67797177, compound

Product 1

HCID 67796524(3S,4S)-4-(1-t-butyldimethylsilyloxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S,4S)-4-(1-t-butyldimethylsilyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2azetidinone (1.0 g) and triethylamine (0.06 ml) in ethyl acetate (50 ml) was hydrogenated under hydrogen atmosphere in the presence of platinum dioxide (0.05 g) at 0°-5° C. for 2 hours. After removal of the catalyst, the filtrate was washed successively with 2 N hydrochloric acid, brine, 5% sodium bicarbonate solution and brine and dried over anhydrous magnesium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-t-butyldimethylsilyloxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone.

Workup

  1. customAfter removal of the catalyst
  2. washthe filtrate was washed successively with 2 N hydrochloric acid, brine, 5% sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-861d024466dd4d4080c9da9b7e68b68d
Source dataset
uspto-grants-1991_12
Patent number
US05075435

Reaction notes

Loading…