Acetohydrazide → HCID 57650280, compound

HRID 2063470Notes

Reaction equation

HRID 2063470 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17](=S)[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]([NH:31][NH2:32])(=O)[CH3:29]>C(#N)C.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:28]([CH3:29])=[N:31][N:32]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14039AcetohydrazideHCID 57650242HCID 57650242, compound

Product 1

HCID 57650280HCID 57650280, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of (2R,4R)-tert-butyl-2-((4-chlorobenzyl)carbamothioyl)-4-acetoxypyrrolidine-1-carboxylate from Step C (1.6 g, 3.88 mmol) and acetic hydrazide (575 mg, 7.76 mmol) in acetonitrile (18 ml) was added mercury (II) acetate (1.85 g, 5.82 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was filtered through a plug of celite and washed with acetonitrile. The combined filtrates were concentrated, the resulting residue taken up in EtOAc (200 ml), then washed with H2O (75 ml), dried (Na2SO4), filtered and concentrated. Flash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc) provided the desired product.

Workup

  1. filtrationThe mixture was filtered through a plug of celite
  2. washwashed with acetonitrile
  3. concentrationThe combined filtrates were concentrated
  4. washwashed with H2O (75 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customFlash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc)

Sources & evidence

ORD record
ord-70c54a21e3f74ad19b699e9cde89c2e8
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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