Isovaleryl chloride → HCID 57675214, compound

HRID 490919Notes

Reaction equation

HRID 490919 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].Cl.[CH2:9]([N:11]1[C:15]2[N:16]=[CH:17][C:18]([C:27]3[O:31][N:30]=[C:29]([CH2:32][CH:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[N:28]=3)=[C:19]([NH:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:14]=2[CH:13]=[N:12]1)[CH3:10].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[CH2:9]([N:11]1[C:15]2[N:16]=[CH:17][C:18]([C:27]3[O:31][N:30]=[C:29]([CH2:32][CH:33]4[CH2:38][CH2:37][N:36]([C:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4])[CH2:35][CH2:34]4)[N:28]=3)=[C:19]([NH:20][CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[C:14]=2[CH:13]=[N:12]1)[CH3:10]

Participants

5

Reactant 3

HCID 66054Isovaleryl chlorideHCID 81531DiisopropylethylamineHCID 67529443HCID 67529443, compound

Product 1

HCID 57675214HCID 57675214, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Isovaleryl chloride (0.04 mmol) was added to a stirred solution of Intermediate 125 (0.033 mmol) and diisopropylethylamine (0.1 mmol) in chloroform (1 ml) at room temperature. After stirring at room temperature for 1.5 h, the reaction mixture was applied to a SPE cartridge (aminopropyl, 1 g) and the cartridge was eluted sequentially with chloroform, 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 cartridge (silica, 1 g) eluting with a gradient of 30-100% ethyl acetate in petroleum ether to afford Example 176. LCMS showed MH+=496, TRET=3.17 min.

Workup

  1. washthe cartridge was eluted sequentially with chloroform, ethyl acetate and methanol
  2. additionFractions containing the desired product
  3. customThe resulting residue was further purified on a SPE cartridge (silica, 1 g)
  4. washeluting with a gradient of 30-100% ethyl acetate in petroleum ether
  5. customto afford Example 176
  6. customMH+=496, TRET=3.17 min.

Sources & evidence

ORD record
ord-f03eda8da05b43dd84fd8d0945ad6999
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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