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

HRID 2054395노트

반응식

HRID 2054395 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bb0d45a815614c2f9340ab7eeb5e137a
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329658B2

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