Hydrochloric Acid → (2-(4-{4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-propylphenyl}piperazin-1-yl)ethyl]-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione

HRID 1038526ノート

反応式

HRID 1038526 の反応式
[F:1][C:2]([F:31])([F:30])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25]O)[CH2:20][CH2:19]2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[CH3:32][C:33]1([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH:47]([CH3:49])[CH3:48])=[CH:42][CH:41]=2)[NH:37][C:36](=[O:38])[NH:35][C:34]1=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.Cl>CN(C)C=O.O>[F:30][C:2]([F:1])([F:31])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:37]3[C:33]([C:40]4[CH:45]=[CH:44][C:43]([O:46][CH:47]([CH3:49])[CH3:48])=[CH:42][CH:41]=4)([CH3:32])[C:34](=[O:39])[NH:35][C:36]3=[O:38])[CH2:20][CH2:19]2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 3052153Hydantoin, 5-(p-isopropoxyphenyl)-5-methyl-HCID 5462977Diethyl azodicarboxylateHCID 866471852-(4-{4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-propylphenyl}piperazin-1-yl)ethanol

生成物 1

HCID 86647186(2-(4-{4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-propylphenyl}piperazin-1-yl)ethyl]-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione収率 26.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-(4-{4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl]-2-propylphenyl}piperazin-1-yl)ethanol (7.8 mg, 0.0170 mmol), 5-methyl-5-(4-(1-methylethoxy)phenyl)imidazolidine-2,4-dione (A11)(15.6 mg, 0.0631 mmol) and triphenylphosphine (15.8 mg, 0.0601 mmol) were dried with a vacuum pump, dissolved in N,N-dimethylformamide (284 μL), added DEAD (23 μL, 0.0167 mmol) under ice-cold conditions, and the mixture was stirred at room temperature for 1 hour. Under ice-cold conditions, the reaction solution was added water (1.0 mL) and 2N aqueous solution of hydrochloric acid (1.0 mL), and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (3.1 mg (yield 26%)) was obtained as a yellow oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

出典と根拠

ORDレコード
ord-fbd7692e9e614daf9f73856e2744e60f
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

反応ノート

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