Water → t-Butyl 1-benzyloxycarbonyl-4-cyclohexylmethylaminocarbonylpiperidin-4-ylcarbamate

HRID 604937ノート

反応式

HRID 604937 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[CH:40]1([CH2:46][NH2:47])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1.O>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:14]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])([C:17]([NH:47][CH2:46][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)=[O:19])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 76688CyclohexanemethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231027164-n-Boc-amino-1-cbz-isonipecotic acid

生成物 1

HCID 67038112t-Butyl 1-benzyloxycarbonyl-4-cyclohexylmethylaminocarbonylpiperidin-4-ylcarbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-benzyloxycarbonyl-4-(t-butoxycarbonylamino)piperidin-4-carboxylic acid (297 mg) in dimethylformamide (2.5 mL) were added 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (226 mg), 4-N,N-dimethylaminopiperidine (144 mg) and cyclohexylmethylamine (0.15 mL) and the solution was stirred at room temperature overnight. Water was added to the reaction mixture, which was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=40:1-10:1) to give the title compound having the following physical data.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=40:1-10:1)

出典と根拠

ORDレコード
ord-59303d587937430cb4be83fd1e5ddab5
出典データセット
uspto-grants-2011_03
特許番号
US07910741B2

反応ノート

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