Sulfuric Acid → 1-Benzhydryl-3-isopropylaminoazetidine-3-carboxylic Acid Amide

HRID 2054395ノート

反応式

HRID 2054395 の反応式
[CH:1]([N:14]1[CH2:17][C:16]([NH:20][CH:21]([CH3:23])[CH3:22])([C:18]#[N:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:24]S(O)(=O)=O>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16]([NH:20][CH:21]([CH3:23])[CH3:22])([C:18]([NH2:19])=[O:24])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 219057861-(Diphenylmethyl)-3-[(propan-2-yl)amino]azetidine-3-carbonitrile

生成物 1

HCID 587216991-Benzhydryl-3-isopropylaminoazetidine-3-carboxylic Acid Amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-benzhydryl-3-isopropylaminoazetidine-3-carbonitrile (I-3A-1a; 3.40 g, 11.1 mmol) in methylene chloride (25 ml) cooled in an ice bath was treated with H2SO4 (5.95 ml, 111 mmol), dropwise. After the reaction mixture was allowed to warm to room temperature and stir overnight, it was cooled in an ice bath and then carefully quenched with concentrated NH4OH to pH 11. The mixture was extracted with methylene chloride, the combined organic layers were dried (Na2SO4) and then concentrated, in vacuo, to afford a crude foam (3.3 g) that was then purified on a Biotage™ Flash 40M column using 0-2% methanol in methylene chloride as eluant to afford the title compound I-3A-1b (2.32 g, 64%) as a brown solid: +ESI MS (M+1) 324.4; 1H NMR (400 MHz, CD3OD) δ 7.40 (d, J=7.5 Hz, 4H), 7.24 (t, J=7.5 Hz, 4H), 7.15 (t, J=7.1 Hz, 2H), 4.46 (s, 1H), 3.53 (d, J=8.7 Hz, 2H), 3.06 (d, J=8.7 Hz, 2H), 2.90 (septuplet, J=6.4 Hz, 1H), 0.97 (d, J=6.6 Hz, 6H).

後処理

  1. temperatureit was cooled in an ice bath
  2. customcarefully quenched with concentrated NH4OH to pH 11
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated, in vacuo
  6. customto afford a crude foam (3.3 g) that
  7. customwas then purified on a Biotage™ Flash 40M column

出典と根拠

ORDレコード
ord-bb0d45a815614c2f9340ab7eeb5e137a
出典データセット
uspto-grants-2008_02
特許番号
US07329658B2

反応ノート

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