Ethyl bromopyruvate → HCID 22381051、化合物

HRID 895706

反応式

HRID 895706 の反応式
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].Br[CH2:11][C:12](=O)[C:13]([O:15]CC)=[O:14].C(=O)(O)[O-].[Na+]>O.C(#N)C>[CH3:4][C:3]1([CH3:5])[CH:2]([C:7]([OH:9])=[O:8])[NH:1][C:12]([C:13]([OH:15])=[O:14])=[CH:11][S:6]1

参加物

6

反応物 3

HCID 66144Ethyl bromopyruvateHCID 92863L-PenicillamineHCID 516892Sodium Bicarbonate

生成物 1

HCID 22381051HCID 22381051、化合物収率 34.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of L-penicillamine (298 mg, 2.0 mmol) in water (5 mL) and acetonitrile (5 mL) was added ethyl 3-bromopyruvate (0.25 mL, 390 mg, 2.0 mmol) slowly. To the resulted mixture was added sodium bicarbonate aqueous solution till the pH about 5. Acetonitrile was removed under vacuum and some more water was added. The solution was extracted with methylene chloride. The water phase was separated and freeze-dried under high vacuum. The residue was chromatographed (silica gel, methylene chloride-methanol-acetic acid 100:5:0.3 to 100:10:0.3) to give 150 mg of product (yield 31%). 1HNMR (300 Hz, D3COD) δ (ppm) 6.17 (s, 1H), 4.23 (q, J=7.1 Hz, 2H), 3.79 (s, 1H), 1.48 (s, 3H), 1.31 (t, J=7.1 Hz, 3H), 1.29 (s, 3H). 13CNMR (75 Hz, D3COD) δ (ppm) 173.8, 164.0, 128.0, 102.4, 64.1, 62.2, 41.2, 28.3, 25.2, 14.7 ppm. MS (ESI) m/z 268 (M+Na, 100), 246 (M+1, 5).

後処理

  1. customAcetonitrile was removed under vacuum
  2. additionsome more water was added
  3. extractionThe solution was extracted with methylene chloride
  4. customThe water phase was separated
  5. customfreeze-dried under high vacuum
  6. customThe residue was chromatographed (silica gel, methylene chloride-methanol-acetic acid 100:5:0.3 to 100:10:0.3)

出典と根拠

ORDレコード
ord-cb77d3d769ad426b93264f6323dd9ee8
出典データセット
uspto-grants-2005_07
特許番号
US06916850B2

関連ノート

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