Hydrochloric Acid → 4-(2,2-Difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochloride salt

HRID 712963ノート

反応式

HRID 712963 の反応式
[ClH:1].[F:2][CH:3]([F:28])[CH2:4][N:5]1[CH2:10][C:9]2([CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[O:8][CH:7]([C:23]2[O:24][CH:25]=[CH:26][N:27]=2)[CH2:6]1>C(Cl)Cl>[ClH:1].[F:28][CH:3]([F:2])[CH2:4][N:5]1[CH2:10][C:9]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[O:8][CH:7]([C:23]2[O:24][CH:25]=[CH:26][N:27]=2)[CH2:6]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86672466Tert-butyl 4-(2,2-difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

生成物 1

HCID 866724644-(2,2-Difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochloride salt収率 94.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

HCl (781 μL of 4 M in dioxane, 3.12 mmol) was added to a solution of tert-butyl 4-(2,2-difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (121 mg, 0.31 mmol) in DCM (0.7 mL) and the reaction mixture was stirred for 1 hour at room temperature. The solvent and excess HCl was removed under reduced pressure and the resulting solid was dissolved in methanol (3 mL) and purified by Waters mass directed LC/MS: (1-99% ACN/H2O (5 mM HCl)). The desired fractions were combined and concentrated in vacuo to yield 4-(2,2-difluoroethyl)-2-(oxazol-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochloride salt (95 mg, 94%) as a white solid. ESI-MS m/z calc. 287.1. found 288.3 (M+1)+; Retention time: 0.96 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 8.15 (d, J=0.8 Hz, 1H), 7.23 (d, J=0.8 Hz, 1H), 6.22 (tt, J=55.1, 4.0 Hz, 1H), 4.94 (dd, J=10.8, 2.6 Hz, 1H), 3.19-2.79 (m, 8H), 2.65-2.54 (m, 2H), 2.25 (dd, J=11.9, 1.5 Hz, 1H), 1.83-1.70 (m, 2H), 1.65 (dd, J=15.1, 3.9 Hz, 1H).

後処理

  1. customThe solvent and excess HCl was removed under reduced pressure
  2. dissolutionthe resulting solid was dissolved in methanol (3 mL)
  3. custompurified by Waters mass
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8787af38e0ae422b8837438d48474828
出典データセット
uspto-grants-2015_11
特許番号
US09181273B2

反応ノート

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