Potassium Carbonate → 4-[4-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenoxy]-butyric acid tert-butyl ester

HRID 1891364

반응식

HRID 1891364 반응식
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([OH:9])=[C:4]([S:10]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]2=3)(=[O:12])=[O:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>CN(C=O)C>[C:37]([O:36][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][O:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([Br:1])=[CH:3][C:4]=1[S:10]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]2[CH:20]=[CH:21][CH:22]=[CH:23][C:14]1=2)(=[O:12])=[O:11])([CH3:40])([CH3:39])[CH3:38]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 684721004-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol

생성물 1

HCID 684692714-[4-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenoxy]-butyric acid tert-butyl ester수율 93.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
62 °C

실험 절차

To 4-bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol (0.83 g, 2 mmol) in dry DMF (8 mL), was added K2CO3 (0.69 g, 5 mmol), followed by the addition of t-butyl 4-bromobutyrate (0.58 g, 2.6 mmol). The mixture was heated at 62° C. for 15 hrs and partitioned between ethyl acetate (50 mL) and water (25 mL). The organic layer was separated, washed with brine (2×25 mL), and dried over MgSO4. After filtration, the solution was concentrated and purified by silica gel column chromatography eluting with ethyl acetate in hexanes (1/8) yielding 4-[4-bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenoxy]-butyric acid tert-butyl ester as a pale yellow foam (1.05 g). MS: 501.8 (M+H-tBu)+; tR=11.2 min (method 2). NMR (CDCl3), δ, 8.060 (1H, s), 7.133-7.205 (3H, m), 7.011-7.067 (1H, m), 6.789 (1H, d, J=8.1 Hz), 4.086 (2H, t), 3.742 (2H, t), 2.826 (2H, m), 2.346 (2H, t), 1.827-1.959 (4H, m), 1.617-1.641 (2H, m), 1.431 (9H, s).

후처리

  1. custompartitioned between ethyl acetate (50 mL) and water (25 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (2×25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with ethyl acetate in hexanes (1/8)

출처 및 근거

ORD 기록
ord-9bdbc997793c47289c3cfa7c7181b0b3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507536B2

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