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

HRID 2054612
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HRID 2054612 반응식
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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 516892Sodium Bicarbonate
용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-35fa26a58be343789152c324d21c3def
출처 데이터셋
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07329727B2

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