Hydrochloric Acid → HCID 57248932, compound

HRID 893174Notes

Reaction equation

HRID 893174 reaction equation
[CH2:1]([CH:10]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[N:11]1[CH:14]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:17])[CH:13]([CH:28]=[CH2:29])[C:12]1=[O:30])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[OH-:40].[Na+].[BH4-].[Na+].Cl>O1CCCC1.C([O-])(=O)C.[Hg+2].C([O-])(=O)C.C(OCC)C.O>[CH2:31]([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]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:17])[CH:13]([CH:28]([OH:40])[CH3:29])[C:12]1=[O:30])[C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 57275515HCID 57275515, compound

Product 1

HCID 57248932HCID 57248932, compound

Reagents, catalysts & solvents 4

HCID 15337Mercuric acetateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

2.85 g of 1-(di-p-anisylmethyl)-3-ethenyl-4-p-methoxybenzyloxycarbonylmethyl-2-azetidinone was dissolved in 14 ml of tetrahydrofuran, and 7 ml of water and 2.0 g of mercury (II) acetate were added thereto, followed by stirring at 35° C. for 5 hours. 12 ml of a 1N aqueous solution of sodium hydroxide was added thereto at 0° C., and to the resulting mixture was then added dropwise a solution of 0.25 g of sodium borohydride in 1 ml of a 1N aqueous solution of sodium hydroxide. After stirring at the same temperature for 15 minutes, the reaction mixture was neutralized with a 2N hydrochloric acid aqueous solution. Diethyl ether was added thereto, followed by filtration using Celite. The filtrate was extracted with diethyl ether, and the extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and distilled off to remove the solvent, thereby to obtain 2.6 g of 1-(di-p-anisylmethyl)-3-(1-hydroxyethyl)-4-p-methoxybenzyloxycarbonylmethyl-2-azetidinone.

Workup

  1. stirringAfter stirring at the same temperature for 15 minutes
  2. filtrationfollowed by filtration
  3. extractionThe filtrate was extracted with diethyl ether
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled off
  7. customto remove the solvent

Sources & evidence

ORD record
ord-54a37225d8544113ad870f432e48bc09
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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