Sodium Hydroxide → (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one

HRID 21709Notes

Reaction equation

HRID 21709 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[O:18])[CH3:16])[NH:13][C:12]1=[O:29])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33].[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)=[O:18])[CH3:16])[N:13]([CH2:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=2)=[O:33])[C:12]1=[O:29])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 70153214-Nitrobenzyl bromoacetateHCID 15223699HCID 15223699, compound

Product 1

HCID 15223718(3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]azetidin-2-one (1.12 g) in methylene chloride (14 ml), there were successively added p-nitrobenzyl alpha-bromoacetate (1.09 g), 50% aqueous sodium hydroxide solution (0.85 g) and triethylbenzylammonium chloride (303 mg), followed by stirring at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted with a mixture of diethyl ether and methylene chloride (3:1) three times. The organic layer was washed successively with water two times and brine three times, dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography to give (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one.

Workup

  1. extractionextracted with a mixture of diethyl ether and methylene chloride (3:1) three times
  2. washThe organic layer was washed successively with water two times and brine three times
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5d4bb3c5cb6b48369981d5bc8b6c8dc2
Source dataset
uspto-grants-1995_06
Patent number
US05424422

Reaction notes

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