Benzoyl chloride → HCID 178499578, compound

HRID 970148Notes

Reaction equation

HRID 970148 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:11])[C@H:8]([OH:17])[C@@H:7]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[N:27][C:28]#[N:29])[C:6]=2[CH:30]=1.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C1COCC1>[C:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:11])[C@H:8]([OH:17])[C@@H:7]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[N:27][C:28]#[N:29])[C:6]=2[CH:30]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178499572HCID 178499572, compound

Product 1

HCID 178499578HCID 178499578, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg (0.24 mmol) of the compound obtained in example 5 was dissolved in 1 ml of THF, then 28 μl (0.24 mmol) of benzoyl chloride and 51 μl (0.37 mmol) of triethylamine were added thereto. The reaction was stirred at room temperature for 2 hours, 10 ml of saturated NaHCO3 solution was added, and aqueous layer was extracted with 20 ml of ethyl acetate. Organic layer was dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2), to give 68 mg (yield: 54%) of the target compound.

Workup

  1. extractionaqueous layer was extracted with 20 ml of ethyl acetate
  2. dry with materialOrganic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-44559e0932e643679f1f2efc9c47860b
Source dataset
uspto-grants-2007_12
Patent number
US07309793B2

Reaction notes

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