Water → HCID 53672631, compound

HRID 325004Notes

Reaction equation

HRID 325004 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][SH:4].O.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>C1(C)C=CC=CC=1.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH2:3]([S:4][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)[CH:2]([CH3:5])[CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 10558Isobutyl mercaptanHCID 12590460(3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one

Product 1

HCID 53672631HCID 53672631, compound

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of zinc acetate (0.7 g, 3 mmol) in toluene (15 mL) and 2-methyl-propanethiol (0.72 g, 8 mmol) was refluxed for 45 min in an apparatus equipped with a Dean-Stark trap to azeotrope water. (3R,4R)-4-(Methylsulfonyl)-3-(triphenylmethylamino)azetidin-2-one (1.5 g, 36 mmol) was added and the mixture was heated to 90° C. for 2 h. The mixture was concentrated and the residue was triturated with ethyl acetate and the insoluble material was removed by filtration. The filtrate was concentrated and the residue was chromatographed on silica gel eluted with 20% ethyl acetate:hexane. The fractions containing the product were combined, concentrated to give the title compound. MS(ES) m/e 417 [M+H]+.

Workup

  1. customequipped with a Dean-Stark trap
  2. concentrationThe mixture was concentrated
  3. customthe residue was triturated with ethyl acetate
  4. customthe insoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed on silica gel
  7. washeluted with 20% ethyl acetate
  8. additionThe fractions containing the product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9bd17e7e9e344de680876d6145c017e8
Source dataset
uspto-grants-2001_04
Patent number
US06221860B1

Reaction notes

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