Hydrochloric Acid → HCID 15223720, compound

HRID 21710Notes

Reaction equation

HRID 21710 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([O:19]CC2C=CC(OC)=CC=2)=[O:18])[CH3:16])[N:13]([CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=2)=[O:31])[C:12]1=[O:43])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[N:13]([CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=2)=[O:31])[C:12]1=[O:43])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2].[OH:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[N:13]([CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([N+:40]([O-:42])=[O:41])=[CH:38][CH:39]=2)=[O:31])[C:12]1=[O:43])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15223718(3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one

Product 2

HCID 15223720HCID 15223720, compoundHCID 15223722HCID 15223722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one (142 mg) in dry methylene chloride, there was BF3 -Et2O complex (163 mg) under ice-cooling, followed by stirring at room temperature. The reaction mixture was poured into a cold aqueous sodium bicarbonate solution, acidified with dilute hydrochloric acid and extracted with ethyl acetate three times. The organic layer was washed successively with dilute hydrochloric acid and brine, 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-carboxyethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one (Compound A) and (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-carboxyethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one (Compound B).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate three times
  3. washThe organic layer was washed successively with dilute hydrochloric acid and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-35ee0b6820d247ea9c22f7c042504b9a
Source dataset
uspto-grants-1995_06
Patent number
US05424422

Reaction notes

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