p-Toluenesulfonic acid → HCID 86601657、化合物

HRID 503679ノート

反応式

HRID 503679 の反応式
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:32][CH2:33][O:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:25]1[CH2:29][O:28]C(C)(C)[O:26]1)=[O:22])(=[O:4])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:38][S:35]([O:34][CH2:33][CH2:32][N:8]([CH2:7][CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[C:21]([NH:23][CH2:24][CH:25]([OH:26])[CH2:29][OH:28])=[O:22])(=[O:36])=[O:37]

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 118014282-(2-({[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]amino}carbonyl){2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate

生成物 1

HCID 86601657HCID 86601657、化合物収率 73.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 2-(2-({[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]amino}carbonyl){2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate (13g) [Palmer et al., J. Med. Chem. 1997, 40, 1272] (5.0 mmol) in MeOH (200 mL) was treated with p-toluenesulfonic acid (0.2 g) at room temperature for 4 h. Most of the MeOH was then evaporated, and the residue was taken up in EtOAc (200 mL), washed with satd. NaHCO3 and brine, dried and concentrated. Chromatography of the product on silica gel, eluting with EtOAc/MeOH (20:1), gave 2-(2-{[(2,3-dihydroxypropyl)amino]carbonyl}{2-[(methylsulfonyl)oxy]ethyl}-4,6-dinitroanilino)ethyl methanesulfonate (13f) (2.0 g, 73%): as yellow foam;

後処理

  1. customMost of the MeOH was then evaporated
  2. washwashed with satd
  3. dry with materialNaHCO3 and brine, dried
  4. concentrationconcentrated
  5. washChromatography of the product on silica gel, eluting with EtOAc/MeOH (20:1)

出典と根拠

ORDレコード
ord-5e2489af56df4112bfc9efe5111f8a7f
出典データセット
uspto-grants-2010_08
特許番号
US07776924B2

反応ノート

読み込み中…