4-Toluenesulfonyl chloride → HCID 68580031, compound

HRID 2233903Notes

Reaction equation

HRID 2233903 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([NH:28][NH:29][C:30](=[O:35])[C:31]([O:33][CH3:34])=[O:32])=O)[CH2:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:21][CH2:22][N:23]([C:26]2[O:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[N:29][N:28]=2)[CH2:24][CH2:25]1)=[O:18])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86608264HCID 86608264, compound2×

Product 1

HCID 68580031HCID 68580031, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TEA (0.20 ml, 1.34 mmol), para-toluenesulfonyl chloride (255 mg, 1.34 mmol), methyl [2-({4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}carbonyl)hydrazino](oxo)acetate (Intermediate 157) (460 mg, 1.34 mmol) and DCM (8 ml) were combined and stirred overnight. The mixture was diluted with DCM (150 ml) and washed with water (10 ml). The organic phase was separated, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash column chromatography (DCM/acetone, 8:1 ratio with 1% MeOH) to yield 342 mg of the title compound.

Workup

  1. washwashed with water (10 ml)
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography (DCM/acetone, 8:1 ratio with 1% MeOH)

Sources & evidence

ORD record
ord-90698c2cecb74353ad446e3339d4f3b2
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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