5-Chlorovaleryl chloride → HCID 57675182, compound

HRID 490910Notes

Reaction equation

HRID 490910 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[NH2:9][CH2:10][C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[N:20][C:19]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:18]=3[C:17]=2[NH:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[O:13][N:12]=1.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:9][CH2:10][C:11]1[N:15]=[C:14]([C:16]2[C:17]([NH:27][CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[C:18]3[CH:24]=[N:23][N:22]([CH2:25][CH3:26])[C:19]3=[N:20][CH:21]=2)[O:13][N:12]=1)=[O:7]

Participants

5

Reactant 3

HCID 740895-Chlorovaleryl chlorideHCID 81531DiisopropylethylamineHCID 57675147HCID 57675147, compound

Product 1

HCID 57675182HCID 57675182, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-chloropentanoyl chloride (0.12 mmol) was added to a stirred solution of Intermediate 118 (0.1 mmol) and diisopropylethylamine (0.3 mmol) in chloroform (1 ml) at room temperature. After stirring at room temperature for 16 h, the reaction mixture was applied to a SPE cartridge (aminopropyl, 2 g) and the cartridge was eluted sequentially with chlororm, ethyl acetate and methanol. Fractions containing the desired product were combined and blown down under nitrogen. The resulting residue was further purified on a SPE cartidge (silica, 1 g) eluting with a gradient of 30-100% ethyl acetate in petroleum ether to afford Intermediate 120 as a white solid (46 mg). LCMS showed MH+=462, TRET=2.86 min.

Workup

  1. washthe cartridge was eluted sequentially with chlororm, ethyl acetate and methanol
  2. additionFractions containing the desired product
  3. customThe resulting residue was further purified on a SPE cartidge (silica, 1 g)
  4. washeluting with a gradient of 30-100% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ebb4b2473939429e9807a30ea54c43d7
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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