Diisopropylethylamine → 2-(dimethylamino)-2-oxoethyl (3S)-2-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-8-(2,2-dimethylpropyl)-2,8-diazaspiro[4.5]decane-3-carboxylate

HRID 445238노트

반응식

HRID 445238 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:39]=[CH:38][C:18]([CH2:19][N:20]2[C@H:24]([C:25]([OH:27])=[O:26])[CH2:23][C:22]3([CH2:32][CH2:31][N:30]([CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:29][CH2:28]3)[CH2:21]2)=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.O[CH2:41][C:42]([N:44]([CH3:46])[CH3:45])=[O:43].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C@H:24]([C:25]([O:27][CH2:41][C:42]([N:44]([CH3:46])[CH3:45])=[O:43])=[O:26])[CH2:23][C:22]3([CH2:32][CH2:31][N:30]([CH2:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:29][CH2:28]3)[CH2:21]2)=[CH:38][CH:39]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 67285755(3S)-2-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-8-(2,2-dimethylpropyl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

생성물 1

HCID 866644662-(dimethylamino)-2-oxoethyl (3S)-2-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-8-(2,2-dimethylpropyl)-2,8-diazaspiro[4.5]decane-3-carboxylate수율 73.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To an N,N-dimethylformamide (1 mL) solution of the compound (80 mg) obtained in Example 32(5), 2-hydroxy-N,N-dimethylacetoamide (CAS Registry Number: 14658-93-6; 77 mg), diisopropylethylamine (39 μL) and N,N,N′,N′-tetramethyl-O-(7-azobenzotriazol-1-yl)uronium hexafluorophosphate (86 mg) were added. The reaction solution was stirred at room temperature for 16 hours. To this solution, an aqueous saturated sodium hydrogen carbonate solution was added, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CHROMATOREX NH (trade name), manufactured by Fuji Silysia Chemical Ltd.) (ethyl acetate:methanol=1:0→30:1→15:1) to obtain the title compound (68 mg) having the following physical properties.

후처리

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (CHROMATOREX NH (trade name), manufactured by Fuji Silysia Chemical Ltd.) (ethyl acetate:methanol=1:0→30:1→15:1)

출처 및 근거

ORD 기록
ord-f426e78d9fcd4042b1142f6aacec342f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476290B2

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