Tetrahydrofuran → HCID 14257300, compound

HRID 622588Notes

Reaction equation

HRID 622588 reaction equation
[CH3:1][S:2]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)=O.[O:30]1[CH2:34]CC[CH2:31]1.[OH-:35].[Na+]>CO>[CH3:31][O:30][C:34]([CH2:1][S:2][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:35]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12590460(3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one

Product 1

HCID 14257300HCID 14257300, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10 g of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone in 250 ml of methanol is added 100 ml of tetrahydrofuran, followed by addition of 3.45 g of methyl thioglycollate and 32.5 ml of 1N sodium hydroxide under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. The solvent is then distilled off under reduced pressure and 100 ml of ethyl acetate is added. The ethyl acetate layer is separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography using n-hexane-ethyl acetate (3:2). The earlier eluate fractions are combined and concentrated under reduced pressure to give 4.35 g of (3R,4R)-4-[[(methoxycarbonyl)methyl]thio]-3-tritylamino-2-azetidinone.

Workup

  1. temperaturecooling
  2. distillationThe solvent is then distilled off under reduced pressure and 100 ml of ethyl acetate
  3. additionis added
  4. customThe ethyl acetate layer is separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b620e0c17b084c2092108173af991335
Source dataset
uspto-grants-1988_09
Patent number
US04771045

Reaction notes

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