Tert-butyl acetoacetate → HCID 86643503、化合物

HRID 1891378ノート

反応式

HRID 1891378 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH2:22].[C:23](OC(C)(C)C)(=[O:28])[CH2:24][C:25]([CH3:27])=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:9])=[O:10])=[CH:4][C:3]=1[NH:22][C:23](=[O:28])[CH2:24][C:25](=[O:26])[CH3:27]

参加物

4

反応物 2

HCID 15538Tert-butyl acetoacetateHCID 231203012-Chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine

生成物 1

HCID 86643503HCID 86643503、化合物収率 79.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To 2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine (1.0 g, 3 mmol, step 4B) in dry toluene (60 mL) was added tert-butyl acetoacetate (0.75 mL, 4.5 mmol) and 4-dimethyl-aminopyridine (0.37 g, 3 mmol). The mixture was refluxed under N2 for 16 hrs. After the removal of toluene, the reaction residue was repartitioned with ethyl acetate (100 mL) and water (50 mL). The organic layer was washed with sat. NH4Cl (2×50 mL) and brine (2×50 mL) and was dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (3/1 to 1/1) yielded N-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-3-oxo-butyramide as yellowish solid (1.0 g). MS: 421.0 (M+H)+; tR=2.74 min (method 1).

後処理

  1. temperatureThe mixture was refluxed under N2 for 16 hrs
  2. customAfter the removal of toluene
  3. washThe organic layer was washed with sat. NH4Cl (2×50 mL) and brine (2×50 mL)
  4. dry with materialwas dried over MgSO4
  5. concentrationConcentration and purification by silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (3/1 to 1/1)

出典と根拠

ORDレコード
ord-761a1d6d680f422cb2db7baf74a2ac95
出典データセット
uspto-grants-2013_08
特許番号
US08507536B2

反応ノート

読み込み中…