Tert-butyl acetoacetate → HCID 86643503, compound

HRID 1891378Notes

Reaction equation

HRID 1891378 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH2:22].[C:23](OC(C)(C)C)(=[O:28])[CH2:24][C:25]([CH3:27])=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:9])=[O:10])=[CH:4][C:3]=1[NH:22][C:23](=[O:28])[CH2:24][C:25](=[O:26])[CH3:27]

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 231203012-Chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine

Product 1

HCID 86643503HCID 86643503, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine (1.0 g, 3 mmol, step 4B) in dry toluene (60 mL) was added tert-butyl acetoacetate (0.75 mL, 4.5 mmol) and 4-dimethyl-aminopyridine (0.37 g, 3 mmol). The mixture was refluxed under N2 for 16 hrs. After the removal of toluene, the reaction residue was repartitioned with ethyl acetate (100 mL) and water (50 mL). The organic layer was washed with sat. NH4Cl (2×50 mL) and brine (2×50 mL) and was dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (3/1 to 1/1) yielded N-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-3-oxo-butyramide as yellowish solid (1.0 g). MS: 421.0 (M+H)+; tR=2.74 min (method 1).

Workup

  1. temperatureThe mixture was refluxed under N2 for 16 hrs
  2. customAfter the removal of toluene
  3. washThe organic layer was washed with sat. NH4Cl (2×50 mL) and brine (2×50 mL)
  4. dry with materialwas dried over MgSO4
  5. concentrationConcentration and purification by silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (3/1 to 1/1)

Sources & evidence

ORD record
ord-761a1d6d680f422cb2db7baf74a2ac95
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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