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Water → HCID 57073292, compound

HRID 619708
Notes
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Reaction equation

HRID 619708 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@H:24]([O:25][C:26](=O)[CH3:27])[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1COCC1>[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@H:24]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@@H:24]([O:25][C:26]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:27]=2)[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 14798Sodium HydroxideHCID 13124491HCID 13124491, compound

Product 2

HCID 57073292HCID 57073292, compoundHCID 57174922HCID 57174922, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a solution of phenol (2.82 g 30 mmole) in THF (30 ml) and 1N NaOH (26 ml, 26 mmole), (3S, 4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one (5.56 g, 20 mmole) in THF (40 ml) and H2O (20 ml) is added at 0° C. The mixture is stirred at 0° C for 1 hour and then at room temperature for 30 min. After removal of solvent, the residue is dissolved in ethyl acetate, washed with water, brine and dried over sodium sulphate. After removal of solvent, the residue is purified by silica gel column chromatography using hexane-ethyl acetate as eluent. 2.75 g of (3S, 4S)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (A), 890 mg of (3S, 4R)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (B) and 1.08 g of a mixture of (A) and (B) is obtained.

Workup

  1. waitat room temperature for 30 min
  2. customAfter removal of solvent
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate
  6. customAfter removal of solvent
  7. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7d2a6508254449269e856a6bf57e5bdb
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