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Diethyl Ether → S-(2-(2-methoxyethoxy)ethyl)carbonyl-L-cysteine

HRID 2054612
ノート
印刷プレビュー

反応式

HRID 2054612 の反応式
Cl.[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].C[CH2:10][O:11]CC.CO[CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22](Cl)=O>C(=O)(O)[O-].[Na+].O>[CH3:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][C:10]([S:5][CH2:4][C@@H:3]([C:6]([OH:8])=[O:7])[NH2:2])=[O:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 60960Cysteine HydrochlorideHCID 128583902-(2-Methoxyethoxy)ethyl carbonochloridate

生成物 1

HCID 57299832S-(2-(2-methoxyethoxy)ethyl)carbonyl-L-cysteine収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 516892Sodium Bicarbonate
溶媒

反応条件

温度
0 °C

実験手順

L-cysteine hydrochloride (2.00 g, 12.7 mmol) was dissolved in 1M aqueous sodium bicarbonate (25.4 ml) and the solution was diluted with water (75 mL). The solution was cooled in an ice bath and then covered with ether (50 ml). (2-(2-methoxyethoxy)ethyl)chloroformate (2.31 g, 12.7 mmol) was added to the solution in one portion with vigorous stirring for one hour at 0° C. The temperature was allowed to rise to 10° C. and stirred for an additionional two hours. The solvents were then removed under reduced pressure. The resulting solid was washed with methanol and the methanol layer was evaporated to yield the product as a white oil (2.21 g, 65%). FTIR: 1709 cm−1. 1H NMR (D2O): 64.43 (m,11H), 4.24 (m, 2H), 3.83-3.47 (m, 8H), 3.41 (s, 3H).

後処理

  1. temperatureThe solution was cooled in an ice bath
  2. customto rise to 10° C.
  3. stirringstirred for an additionional two hours
  4. customThe solvents were then removed under reduced pressure
  5. washThe resulting solid was washed with methanol
  6. customthe methanol layer was evaporated

出典と根拠

ORDレコード
ord-35fa26a58be343789152c324d21c3def
出典データセット
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07329727B2

反応ノート

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