Hydrochloric Acid → HCID 57059665, compound

HRID 1252207Notes

Reaction equation

HRID 1252207 reaction equation
[CH2:1]([CH:10]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[N:11]1[CH:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:16])[CH:13]([CH:27]=[CH2:28])[C:12]1=[O:29])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[O:42]1CCCC1>O.[OH-].[Na+]>[CH2:30]([CH:10]([CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[N:11]1[CH:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:16])[CH:13]([CH:27]([OH:42])[CH3:28])[C:12]1=[O:29])[C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57277964HCID 57277964, compound

Product 1

HCID 57059665HCID 57059665, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A mixture of 1-(di-p-anisylmethyl)-3-ethenyl-4-p-methoxybenzyloxycarbonyl-2-azetidinone (10 g) and mercuric acetate (6.6 g) in terahydrofuran (40 ml) and water (20 ml) was stirred at room temperature for 5 hours. The reaction mixture was treated with 1N aqueous sodium hydroxide (40 ml) and then sodium borohydride (0.78 g) in 1N aqueous sodium hydroxide (2 ml) at ~0° C. The mixture was acidified with 2N hydrochloric acid, filtered to remove any insoluble materials. The filtrate was extracted with diethyl ether. The extract was washed successively with water and aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 1-(di-p-anisylmethyl)-3-(1-hydroxyethyl)-4-p-methoxybenzyloxycarbonyl-2-azetidinone.

Workup

  1. customat ~0° C
  2. filtrationfiltered
  3. customto remove any insoluble materials
  4. extractionThe filtrate was extracted with diethyl ether
  5. washThe extract was washed successively with water and aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customto give an oily residue which
  9. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-6c23f6feece74b25a701383df2928448
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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