2-Mercaptoethanol → HCID 54219948, compound

HRID 622591Notes

Reaction equation

HRID 622591 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[OH-].[Na+].CS([C@H:11]1[NH:14][C:13](=[O:15])[C@H:12]1[NH:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([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)(=O)=O>O1CCCC1>[OH:4][CH2:3][CH2:2][S:1][C@H:11]1[NH:14][C:13](=[O:15])[C@H:12]1[NH:16][C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 12590460(3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one

Product 1

HCID 54219948HCID 54219948, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, 2.58 g of 2-mercaptoethanol and 33 ml of 1N sodium hydroxide are added to a solution of 12.2 g of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone in 150 ml of tetrahydrofuran, and the mixture is stirred for 30 minutes. The solvent is then distilled off under reduced pressure and 150 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 ethyl acetate-n-hexane (1:2). The earlier eluate fractions are combined and concentrated under reduced pressure to give 5.6 g of (3R,4R)-4-[[2-(hydroxy)ethyl]thio]-3-tritylamino-2-azetidinone.

Workup

  1. temperatureUnder ice-cooling
  2. distillationThe solvent is then distilled off under reduced pressure and 150 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-be80bd7ea89d44f2ab95c1ceed7d8f12
Source dataset
uspto-grants-1988_09
Patent number
US04771045

Reaction notes

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