Tert-butyl acetoacetate → HCID 86643503, 화합물

HRID 1891378노트

반응식

HRID 1891378 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 86643503HCID 86643503, 화합물수율 79.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-761a1d6d680f422cb2db7baf74a2ac95
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507536B2

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