Hydrochloric Acid → 2-(4-(2-(N-(4-butylbenzyl)methylsulfonamido)ethyl)phenyl)acetic acid

HRID 480276노트

반응식

HRID 480276 반응식
C[O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:7][CH:6]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].Cl>CCOC(C)=O.C(#N)C>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:13]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12][CH2:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:2])=[O:18])=[CH:6][CH:7]=2)=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH3:30]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 121508404-Butylbenzyl BromideHCID 23594256[4-[2-Methanesulfonylamino-ethyl]-phenyl]-acetic acid methyl ester

생성물 1

HCID 222467652-(4-(2-(N-(4-butylbenzyl)methylsulfonamido)ethyl)phenyl)acetic acid

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of [4-[2-methanesulfonylamino-ethyl]-phenyl]-acetic acid methyl ester (38 mg, 0.14 mmol), 1-bromomethyl-4-butylbenzene (35 mg, 0.15 mmol), K2CO3 (25 mg, 0.182 mmol) and acetonitrile was heated at reflux for 1 h. Aqueous HCl (2 mL, 1N) and EtOAc (30 mL) were added to the reaction. The organic solution was dried with MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (30% EtOAc/hexanes) to afford the title compound of Step A. 1H NMR (400 MHz, CDCl3) δ 7.28-7.05 (m, 8H), 4.37 (s, 2H), 3.65 (s, 3H), 3.58 (s, 2H), 3.26 (t, 2H), 2.77 (t, 2H), 2.69 (s, 3H), 2.60 (t, 2H), 1.59 (m, 2H), 1.37 (m, 2H), 0.94 (t, 3H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. dry with materialThe organic solution was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography (30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-282020bc3bfe4ae8ba8865f3c8669bf6
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649657B2

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