Water → HCID 22812920, compound

HRID 224547Notes

Reaction equation

HRID 224547 reaction equation
[CH2:1]([O:4][C@H:5]1[N:8]([C:9](=[C:26]([CH3:28])[CH3:27])[C:10]([O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:29])[C@@H:6]1[NH:30][C:31](=[O:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:2]#[CH:3].[OH2:40]>CO.S(=O)(=O)(O)O.C(OCC)(=O)C>[CH2:1]([O:4][C@H:5]1[N:8]([C:9](=[C:26]([CH3:28])[CH3:27])[C:10]([O:12][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:11])[C:7](=[O:29])[C@@H:6]1[NH:30][C:31](=[O:39])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:2]([CH3:3])=[O:40]

Participants

6

Reactant 2

HCID 962WaterHCID 22812924HCID 22812924, compound

Product 1

HCID 22812920HCID 22812920, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diphenylmethyl α-[4(R)-propargyloxy-3(R)-phenylacetamido-2-oxo-azetidin-1-yl]-α-isopropylideneacetate (2.236 g; 4.28 mmole) in methanol (20 ml) is added water (2 ml). To this solution is added a saturated solution of mercuric sulfate in 10% sulfuric acid (0.8 ml), and the mixture is refluxed for 30 minutes. The reaction mixture is cooled, diluted with ethyl acetate, and washed with water. The ethyl acetate layer is dried over sodium sulfate, and concentrated under reduced pressure. Purification of the residue by chromatography over silica gel containing 10% water (100 g) using a mixture of benzene and ethyl acetate (2:1) as eluting solvent gives the product.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by chromatography over silica gel containing 10% water (100 g)
  7. additiona mixture of benzene and ethyl acetate (2:1)
  8. washas eluting solvent
  9. customgives the product

Sources & evidence

ORD record
ord-5625ec6ed415484ea73634eeebb8d097
Source dataset
uspto-grants-1980_11
Patent number
US04233216

Reaction notes

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