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

HRID 72879노트

반응식

HRID 72879 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-938d3cc21835491c85aff4ce0e618f03
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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