1,2-Dichloroethane → HCID 58677920、化合物

HRID 1669837ノート

反応式

HRID 1669837 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=C[C:20]2[N:25]([OH:26])N=NC=2C=1.[CH3:27]CN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:25]([O:26][CH3:27])[CH3:20])=[O:12])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27356093-(4-Bromophenyl)propionic acid

生成物 1

HCID 58677920HCID 58677920、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 24.95 g 3-(4-bromophenyl)propionic acid, 12.75 g N, O-dimethylhydroxylamine hydrochloride, 27.14 g EDC, and 17.66 g HOBt were added 300 mL DMF and 47.4 mL DIEA. The reaction mixture was stirred at room temperature for 17 hours and then poured into 700 mL ice water, extracted with 5×200 mL EtOAc. The combined EtOAc solution was washed with 200 mL 5% NaHCO3, 4×200 mL water, and 200 mL saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give crude product as a yellow oil. It was purified on silica gel using 35˜55% EtOAc in hexanes to give the title compound as yellowish oil. 1H NMR (CDCl3, 500 MHz) δ 7.40˜7.43 (m, 2H), 7.11˜7.14 (m, 2H), 3.63 (s, 3H), 3.19 (s, 3H), 2.93 (t, J=7.8 Hz, 2H), 2.73 (t, J=7.7 Hz, 2H). LC-MS: 1.77 min. (M+H=272.1/274).

後処理

  1. extractionextracted with 5×200 mL EtOAc
  2. washThe combined EtOAc solution was washed with 200 mL 5% NaHCO3, 4×200 mL water, and 200 mL saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give crude product as a yellow oil
  6. customIt was purified on silica gel using 35˜55% EtOAc in hexanes

出典と根拠

ORDレコード
ord-771661e3518145548cdc082f9a0c28ac
出典データセット
uspto-grants-2011_08
特許番号
US07989475B2

反応ノート

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