Benzenepropanoyl chloride → HCID 71059991, compound

HRID 337223Notes

Reaction equation

HRID 337223 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17](=[O:36])[NH:18][CH:19]1[CH2:24][CH2:23][N:22]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[C:30]([Cl:35])[CH:29]=2)(=[O:27])=[O:26])[CH2:21][CH2:20]1)([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1.C(Cl)Cl>[C:12]([O:16][C:17](=[O:36])[NH:18][CH:19]1[CH2:20][CH2:21][N:22]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:9](=[O:10])[CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:30]([Cl:35])[CH:29]=2)(=[O:27])=[O:26])[CH2:23][CH2:24]1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 86674088HCID 86674088, compound

Product 1

HCID 71059991HCID 71059991, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

3-Phenyl propionyl chloride (0.29 g, 1.76 mmol) was added in one portion to a solution of [1-(4-amino-3-chloro-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.57 g, 1.4 mmol) in Pyridine (5 ml) and the mixture was heated to 60° C. The mixture was stirred at this temperature under a nitrogen atmosphere for 12 hours. After this time the mixture was diluted with DCM (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 98% DCM, 2% Methanol) to give the title compound (0.09 g, 8% yield) as a white powder. Tr=2.41 min, m/z (ES+) (M+Na)+ 545.

Workup

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (elution: 98% DCM, 2% Methanol)

Sources & evidence

ORD record
ord-9d133052e7654ab4b0717fd897cf021b
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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