Hydrochloric Acid → 3-(Isopropylamino)azetidine-3-carboxamide hydrochloride

HRID 2054396노트

반응식

HRID 2054396 반응식
C([N:14]1[CH2:17][C:16]([NH:21][CH:22]([CH3:24])[CH3:23])([C:18]([NH2:20])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:25].CCOCC.O>CO.[OH-].[OH-].[Pd+2]>[ClH:25].[CH:22]([NH:21][C:16]1([C:18]([NH2:20])=[O:19])[CH2:17][NH:14][CH2:15]1)([CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 587216991-Benzhydryl-3-isopropylaminoazetidine-3-carboxylic Acid Amide

생성물 1

HCID 467351463-(Isopropylamino)azetidine-3-carboxamide hydrochloride

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

To a solution of 1-benzhydryl-3-isopropylaminoazetidine-3-carboxylic acid amide (I-3A-1b; 2.28 g, 7.05 mmol) in methanol (100 ml) was added 1M HCl in ether (14.8 ml, 14.8 mmol) and then water (10 ml). After the addition of 20% Pd(OH)2 on carbon (60% water; 1.43 g), the mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature overnight. The mixture was filtered through a pad of Celite®, and then concentrated, in vacuo. The residue was then concentrated, in vacuo, from toluene (2×), acetonitrile (2×) and then methanol to give I-3A-1c (1.59 g, 98%) as a tan solid: +APcI MS (M+1) 158.1; 1H NMR (400 MHz, CD3OD) δ 4.71 (d, J=13.3 Hz, 2H), 4.60 (d, J=13.3 Hz, 2H), 3.49 (septuplet, J=6.6 Hz, 1H), 1.34 (d, J=6.6 Hz, 6H).

후처리

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture was filtered through a pad of Celite®
  4. concentrationconcentrated, in vacuo
  5. concentrationThe residue was then concentrated, in vacuo, from toluene (2×), acetonitrile (2×)
  6. custommethanol to give I-3A-1c (1.59 g, 98%) as a tan solid

출처 및 근거

ORD 기록
ord-a676acfbfe294daa999764848a3406f0
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329658B2

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