Chlorosuccinimide → 3-(1-tert-Butyloxycarbonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

HRID 398402ノート

反応式

HRID 398402 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:19][C:20]2[C:21](=[O:32])[N:22]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:23]=[CH:24][N:25]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:33]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:19][C:20]2[C:21](=[O:32])[N:22]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:23]([Cl:33])=[CH:24][N:25]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 31398Chlorosuccinimide2 回HCID 700234103-(1-tert-Butyloxycarbonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-1-ethoxycarbonylmethylpyrazinone

生成物 1

HCID 700235713-(1-tert-Butyloxycarbonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A stirred solution of 3-(1-tert-butyloxycarbonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-1-ethoxycarbonylmethylpyrazinone from step 8 above (2.0 g, 4.5 mmol) and N-chlorosuccinimide (0.67 g, 5.0 mmol) in CHCl3 was heated to reflux for 6 h. More N-chlorosuccinimide (0.20 g, 1.5 mmol) was added and refluxing was continued for 12 h. The reaction was diluted with CHCl3 and washed with aqueous NaHCO3. The organic phase was separated, dried over Mg SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography using a gradient elution of 25-50% EtOAc:hexanes to give the title compound as an amorphous solid (1.5 g, TLC Rf=0.5, 1:1 EtOAc:hexanes; HPLC RT=7.17 min, method A).

後処理

  1. temperatureto reflux for 6 h
  2. temperaturerefluxing
  3. washwashed with aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over Mg SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography
  9. washa gradient elution of 25-50% EtOAc

出典と根拠

ORDレコード
ord-33dc4ca88968423aa3e7bc8d54b11c39
出典データセット
uspto-grants-2003_08
特許番号
US06610692B1

反応ノート

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