Water → HCID 54324264, compound

HRID 1267917Notes

Reaction equation

HRID 1267917 reaction equation
[Li+].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([Cl:24])=[C:19]([CH:23]=2)C([O-])=O)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.O.C(OCC)(=O)C.O>CN(C)C=O>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([Cl:24])=[C:19]([NH2:39])[CH:23]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 199401P,P-Diphenylphosphinic azideHCID 22728543Water ethylacetateHCID 70028635HCID 70028635, compound

Product 1

HCID 54324264HCID 54324264, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-chloro-benzoic acid lithium salt (2.1 g) in N,N-dimethylformamide (50 ml) was added diphenyl phosphorylazide (1.4 ml) and reaction mixture stirred at ambient temperature for 1 hour. Water (30 ml) was added and the reaction mixture heated to 60° C. for 2 hours. After cooling to room temperature, the reaction was poured into ethyl acetate/water, the organic layer separated, washed with water, aqueous NaHCO3 and brine. The organic layer was dried (MgSO4) and concentrated. Purification of the residue by silica gel chromatography (eluting ethyl acetate/iso-hexane (1:3 to 1:1) gave the subtitle product (1.5 g).

Workup

  1. temperaturethe reaction mixture heated to 60° C. for 2 hours
  2. temperatureAfter cooling to room temperature
  3. customthe organic layer separated
  4. washwashed with water, aqueous NaHCO3 and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel chromatography (
  8. washeluting ethyl acetate/iso-hexane (1:3 to 1:1)

Sources & evidence

ORD record
ord-79cb33d8ce114dfabbebb9cf883e5d9c
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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