4-Chlorobutyryl chloride → HCID 57675221, compound

HRID 490909Notes

Reaction equation

HRID 490909 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][CH2:9][C:10]1[N:14]=[C:13]([C:15]2[CH:20]=[N:19][C:18]3[N:21]([CH2:24][CH3:25])[N:22]=[CH:23][C:17]=3[C:16]=2[NH:26][CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[O:12][N:11]=1.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:8][CH2:9][C:10]1[N:14]=[C:13]([C:15]2[C:16]([NH:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[C:17]3[CH:23]=[N:22][N:21]([CH2:24][CH3:25])[C:18]3=[N:19][CH:20]=2)[O:12][N:11]=1)=[O:6]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 81531DiisopropylethylamineHCID 57675147HCID 57675147, compound

Product 1

HCID 57675221HCID 57675221, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-chlorobutanoyl 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 119 as a white solid (45 mg).). LCMS showed MH+=448, TRET=2.77 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-daf171a1ff8d4dcab21a903adaffb108
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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