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

HRID 480276ノート

反応式

HRID 480276 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-282020bc3bfe4ae8ba8865f3c8669bf6
出典データセット
uspto-grants-2003_11
特許番号
US06649657B2

反応ノート

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