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Phenol → (3S,4S)-3-{N-benzyloxycarbonyl-beta-(2-naphthyl)-L-alanyl}-amino-4-phenoxy-azetidin-2-one

HRID 619705
Notes
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Reaction equation

HRID 619705 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([O:15][C:16]([NH:18][C@H:19]([C:31]([C@@H:33]1[C@H:36](OC(=O)C)[N:35]([NH2:41])[C:34]1=[O:42])=[O:32])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1COCC1>CC(C)=O.[OH-].[Na+]>[CH2:8]([O:15][C:16]([NH:18][C@H:19]([C:31]([C@@H:33]1[C@H:36]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:35]([NH2:41])[C:34]1=[O:42])=[O:32])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 996PhenolHCID 8028TetrahydrofuranHCID 86754557(3S,4S)-3-{N-benzyloxycarbonyl-beta-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one

Product 1

HCID 86754556(3S,4S)-3-{N-benzyloxycarbonyl-beta-(2-naphthyl)-L-alanyl}-amino-4-phenoxy-azetidin-2-oneYield 44.2%

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
2×
HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of phenol (30 mg, 0.32 mmol) in acetone (2 ml) and 1 N NaOH (0.25 ml), (3S,4S)-3{N-benzyloxycarbonyl-β-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one (95 mg, 0.2 mmol) in acetone (1 ml) and THF (2 ml) was added at 5° C. The mixture was stirred at 5° C. for 1 hr and then at room temperature for 1 hr. After removal of solvent, the residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:2) as eluent and 45 mg of (3S,4S)-3-{N-benzyloxycarbonyl-β-(2-naphthyl)-L-alanyl}-amino-4-phenoxy-azetidin-2-one was obtained.

Workup

  1. waitat room temperature for 1 hr
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa131022351b4df78380d10e2d7de6bd
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05959123

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes