Sodium Hydroxide → HCID 178468418、化合物

HRID 333419ノート

反応式

HRID 333419 の反応式
FC(F)(F)C(O)=O.[CH:8]1([C:14]2([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:47]([N:49]([CH2:66][CH2:67][C:68]1[N:69]=[CH:70][NH:71][CH:72]=1)[C:50](=[O:65])[NH:51][CH:52]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][CH:58]=1)[C:53](O)=[O:54])[CH3:48].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>ClCCl.CN(C)C=O>[CH:8]1([C:14]2([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][CH2:16][N:17]([C:53](=[O:54])[CH:52]([NH:51][C:50]([N:49]([CH2:47][CH3:48])[CH2:66][CH2:67][C:68]3[N:69]=[CH:70][NH:71][CH:72]=3)=[O:65])[CH2:56][C:57]3[CH:58]=[CH:59][C:60]([O:63][CH3:64])=[CH:61][CH:62]=3)[CH2:18][CH2:19]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

参加物

8

反応物 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66987862Ethyl 4-cyclohexylpiperidine-4-carboxylate trifluoroacetateHCID 178463865HCID 178463865、化合物

生成物 1

HCID 178468418HCID 178468418、化合物収率 30.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

66 mg (0.19 mmol) of ethyl 4-cyclohexylpiperidine-4-carboxylate trifluoroacetate are diluted in 3 mL of dichloromethane and 3 mL of dimethylformamide, and 67 mg (0.21 mmol) of TBTU and 75 mg (0.21 mmol) of 2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionic acid and 0.06 mL (0.38 mmol) of diisopropylethylamine are added. After 2 hours of stirring at room temperature, aqueous 1N NaOH solution is added and the organic products are extracted with dichloromethane. The organic phase is dried and then evaporated. The crude product obtained is chromatographed on silica gel (eluent: 95/5 dichloromethane/methanol). 34 mg of ethyl 4-cyclohexyl-1-[2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate in the form of a yellow oil are obtained in a yield of 30%.

後処理

  1. extractionthe organic products are extracted with dichloromethane
  2. customThe organic phase is dried
  3. customevaporated
  4. customThe crude product obtained
  5. customis chromatographed on silica gel (eluent: 95/5 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-711ed4cda52643c590fffc6db535f3dc
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

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