Hydrochloric Acid → N-((1S,3S,4R)-3-amino-4-ethylcyclopentyl)cyclopropanesulfonamide hydrochloride

HRID 1969815ノート

反応式

HRID 1969815 の反応式
[CH2:1]([C@H:3]1[C@@H:7]([N:8]=C=O)[CH2:6][C@@H:5]([NH:11][S:12]([CH:15]2[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH2:4]1)[CH3:2].[ClH:18].CCOCC.CCOC(C)=O>O>[ClH:18].[NH2:8][C@@H:7]1[C@H:3]([CH2:1][CH3:2])[CH2:4][C@H:5]([NH:11][S:12]([CH:15]2[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH2:6]1

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 58557883N-((1S,3R,4S)-3-ethyl-4-isocyanatocyclopentyl)cyclopropanesulfonamide

生成物 1

HCID 67997976N-((1S,3S,4R)-3-amino-4-ethylcyclopentyl)cyclopropanesulfonamide hydrochloride収率 85%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of N-((1S,3R,4S)-3-ethyl-4-isocyanatocyclopentyl)cyclopropanesulfonamide (0.972 g, 3.76 mmol) and aqueous HCl (6 N, 31.4 mL, 188 mmol) was heated at about 100° C. for about 60 h. Aqueous HCl (12 N, 5 mL) was added and the reaction mixture was heated at about 100° C. for about 18 h. The reaction mixture was cooled to ambient temperature and concd under reduced pressure. The residue was treated with Et2O (10 mL) and EtOAc (10 mL). The mixture was concd under reduced pressure. Water (5 mL) was added and the sample was lyophilized to give N-((1S,3S,4R)-3-amino-4-ethylcyclopentyl)cyclopropane-sulfonamide hydrochloride (0.859 g, 85%) as a white solid: LC/MS (Table 1, Method a) Rt=1.28 min; MS m/z 233 (M+H)+.

後処理

  1. temperaturethe reaction mixture was heated at about 100° C. for about 18 h
  2. temperatureThe reaction mixture was cooled to ambient temperature

出典と根拠

ORDレコード
ord-7af389feb57d4fc985f1fe65bbe68caf
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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