Dimethylformamide → HCID 58043101, compound

HRID 1035189Notes

Reaction equation

HRID 1035189 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CS(O[CH:23]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:23]3[CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateHCID 15576447HCID 15576447, compound

Product 1

HCID 58043101HCID 58043101, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

In a microwave vial, 4-[(4-acetylpiperazin-1-yl)methyl]phenol (1.0 g, 4.3 mmol)—see EP 50298—, tert-butyl 3-[(methylsulfonyl)oxy]azetidine-1-carboxylate (1.0 g, 4.0 mmol) and Cs2CO3 (1.5 g, 4.6 mmol) together with DMF (10 mL) was added. The mixture was heated in a microwave oven at 140° C. for 60 minutes. Water (40 mL) was added and the suspension was extracted with twice with EtOAc (50 mL). The combined organic phases were washed with brine, dried (Na2CO3) and the solvent was removed by evaporation. The residue was co-evaporated with toluene. There was obtained 1.5 g (68%) of 23A.

Workup

  1. extractionthe suspension was extracted with twice with EtOAc (50 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2CO3)
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-7460c39fabf04c98965e433af5f6115f
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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