Methyl iodide → tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

HRID 1455410ノート

反応式

HRID 1455410 の反応式
[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([CH2:25][OH:26])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I[CH3:29]>CN(C)C=O.[Ag]=O>[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C@H:10]([CH2:25][O:26][CH3:29])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 6328Methyl iodideHCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate

生成物 1

HCID 68766937tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6228Dimethylformamide溶媒

実験手順

(1R,3R,4S)-(4-benzyloxycarbonylamino-3-hydroxymethyl-cyclohexyl)carbamic acid tert-butyl ester (1.8 g) was dissolved in N,N-dimethylformamide (15 mL). Iodomethane (50 mL) was added, followed by silver oxide (5.52 g), and the mixture was stirred at room temperature overnight. The mixture was filtered through Celite and the solids were washed with ethyl acetate. The filtrate was washed sequentially with water and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography to provide (1R,3R,4S)-(4-benzyloxycarbonylamino-3-methoxymethylcyclohexyl)carbamic acid tert-butyl ester as a colorless gum (1.78 g). MS found: (M+H)+=393.

後処理

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed with ethyl acetate
  3. washThe filtrate was washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-47b9fa7fc24e4fdabb2b06b07d342251
出典データセット
uspto-grants-2009_01
特許番号
US07482335B2

反応ノート

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