Chlorosuccinimide → HCID 24765971, compound

HRID 1255148Notes

Reaction equation

HRID 1255148 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH:12]=O)[N:11]=1)=[O:5].Cl.[NH2:30][OH:31].C([O-])(O)=O.[Na+].[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39].ClN1C(=O)CCC1=O>CC(O)C.O.C(OCC)(=O)C>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[C:10]([C:12]2[CH:42]=[C:41]([Si:38]([CH3:40])([CH3:39])[CH3:37])[O:31][N:30]=2)[N:11]=1)=[O:5]

Participants

10

Reactant 5

HCID 31398ChlorosuccinimideHCID 66111TrimethylsilylacetyleneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 24765490HCID 24765490, compound

Product 1

HCID 24765971HCID 24765971, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Into a solution of Compound 67 (206 mg, 0.50 mmol) in 2-propanol (1.0 mL) was added hydroxylamine hydrochloride (35 mg, 0.50 mmol). Water was added (4 drops). The mixture was heated to 80° C. for 1 hour, cooled to room temperature, concentrated under reduced pressure. The residue was taken up in ethyl acetate (4.0 mL). The mixture was cooled to 0° C. Into the mixture, water (4 drops), NaHCO3 (84 mg, 1.0 mmol), trimethylsilyl acetylene (0.50 mL, 3.60 mmol), and N-chlorosuccinimide (134 mg, 1.00 mmol) were added sequentially. The mixture was stirred at room temperature overnight, diluted with ethyl acetate, washed with water then with brine, and dried (Na2SO4), filtered and concentrated. The residue was purified on silica to give Compound 105 (110 mg).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. temperatureThe mixture was cooled to 0° C
  4. washwashed with water
  5. dry with materialwith brine, and dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica

Sources & evidence

ORD record
ord-dae6ef1a31fb4754ab609d5dc57c86c0
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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