Hydrochloric Acid → Tert-butyl 3-amino-3-(pyrimidin-2-yl)azetidine-1-carboxylate hydrochloride

HRID 509559ノート

反応式

HRID 509559 の反応式
CC(C)(S([NH:6][C:7]1([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=O)C.[ClH:25].CCOCC>CO>[ClH:25].[NH2:6][C:7]1([C:18]2[N:19]=[CH:20][CH:21]=[CH:22][N:23]=2)[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 89825281Tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-(pyrimidin-2-yl)azetidine-1-carboxylate

生成物 1

HCID 89825528Tert-butyl 3-amino-3-(pyrimidin-2-yl)azetidine-1-carboxylate hydrochloride収率 87%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 3-(1,1-dimethylethylsulfinamido)-3-(pyrimidin-2-yl)azetidine-1-carboxylate (40 mg, 0.113 mmol) in MeOH (0.5 ml) in a 10 ml round-bottomed flask was cooled to 0° C. A solution of HCl in ether (0.141 ml, 0.564 mmol, 4 N) was added. The mixture was then stirred at 0° C. for 15 min and then concentrated at room temperature. The residue was triturated with hexane and diethyl ether. The resulting solid was allowed to settle and supernatant liquid was decanted. The solid obtained was dried under vacuo to afford tert-butyl 3-amino-3-(pyrimidin-2-yl)azetidine-1-carboxylate hydrochloride Yield: 28 mg (87%). 1H NMR (400 MHz, DMSO-d6): δ 9.08 (bs, 2H), 9.0 (d, J=4.8 Hz, 2H), 7.63 (t, J=4.8 Hz, 1H), 4.23-4.21 (m, 4H), 1.43 (s, 9H). LCMS: (ES+) m/z observed=151.2 (M+H)+ of 3-(pyrimidin-2-yl)azetidin-3-amine

後処理

  1. concentrationconcentrated at room temperature
  2. customThe residue was triturated with hexane and diethyl ether
  3. customsupernatant liquid was decanted
  4. customThe solid obtained
  5. customwas dried under vacuo

出典と根拠

ORDレコード
ord-2f47f937b80447858d59117c9582a936
出典データセット
uspto-grants-2015_08
特許番号
US09096580B2

反応ノート

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