Water → HCID 70095013, compound

HRID 1603250Notes

Reaction equation

HRID 1603250 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:20]([CH:22]2[CH:25](OC(=O)C)[N:24]([NH2:30])[C:23]2=[O:31])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:32]1([OH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>C1C=CC=CC=1.C1(C)C=CC=CC=1.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:20]([C@@H:22]2[C@H:25]([O:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:24]([NH2:30])[C:23]2=[O:31])=[O:21])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 996PhenolHCID 131721454HCID 131721454, compound

Product 1

HCID 70095013HCID 70095013, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 2724192Zinc acetate (USP)CatalystHCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

A mixture of (3S,4S)-3-{(N-(3-phenylpropionoyl)-L-phenylalanyl}-amino-4-acetoxy-azetidin-2-one (212 mg, 0.5 mmol) obtained in example 10, phenol (41 mg, 0.45 mmol), and zinc acetate dihydrate (110 mg, 0.5 mmol) in a mixture of benzene (8 ml) and toluene (8 ml) was refluxed for 5.5 hrs using Dean-Stark water separator. The reaction mixture was purified by silica gel column chromatography using hexane-ethyl acetate (2:1) as eluent and the title compound (50 mg) was obtained as a white solid.

Workup

  1. temperaturewas refluxed for 5.5 hrs
  2. customThe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-221fd27552644c9c9b1be15a789cd959
Source dataset
uspto-grants-1999_11
Patent number
US05986108

Reaction notes

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