Methyl iodide → HCID 76850178、化合物

HRID 1171962ノート

反応式

HRID 1171962 の反応式
IC.[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][C:16]#[N:17])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:18]1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:18][O:13][C:12](=[O:14])[C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:15][C:16]#[N:17]

参加物

8

反応物 4

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 7019873Boc-beta-cyano-L-alanine

生成物 1

HCID 76850178HCID 76850178、化合物収率 86.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Iodomethane (2.18 ml, 35.01 mmol) was added to a mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (5.00 g, 23.34 mmol) and DBU (3.67 ml, 24.51 mmol) in toluene (20 mL) at rt. The reaction was stirred at 50 C for 2 days. Water (20 mL), saturated KHSO4 (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (hexane:Ethyl acetate=2:1) to give the (S)-methyl-2-(tert-butoxycarbonylamino)-3-cyanopropanoate as white solid (4.6 g, 86%). 1H NMR (400 MHz, d6-DMSO) δ7.64 (d, J=8.8 Hz, 1H), 4.39 (m, 1H), 3.66 (s, 3H), 2.96 (dd, J=16.8 Hz & 5.1 Hz, 1H), 2.85 (dd, J=16.8 Hz & 5.2 Hz, 1H), 1.40 (s, 9H).

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by chromatography (hexane:Ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-a49283446fa94e4398bd2209b4db3a85
出典データセット
uspto-grants-2010_11
特許番号
US07829665B2

反応ノート

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