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Ethyl cysteinate hydrochloride → S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine ethyl ester

HRID 1638989
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HRID 1638989 반응식
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3].[O-]CC.[Na+].[Na].[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33]I)[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][S:9][CH2:33][CH2:32][CH:29]1[CH2:28][CH2:27][N:26]([C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])[CH2:31][CH2:30]1)[NH2:7])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 2723617Ethyl cysteinate hydrochlorideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14600697Benzyl 4-(2-iodoethyl)piperidine-1-carboxylate

생성물 1

HCID 14600711S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine ethyl ester수율 92.4%

시약·촉매·용매 1

HCID 702
Ethanol
용매
2회

실험 절차

In a nitrogen gas flow, 8.3 g of L-cysteine ethyl ester hydrochloride is added to a sodium ethoxide solution prepared by adding 2 g of metallic sodium to 80 ml of absolute ethanol. After stirring for 1 hours at room temperature, 80 ml of an ethanol solution containing 18.4 g of 2-(1-benzyloxycarbonyl-4-piperidyl)ethyl iodide is added dropwise to this reaction mixture. After stirring for 1 hour at room temperature, the reaction liquid is concentrated under reduced pressure. To the resulting residue, ice-cold water is added. After extracting with ether, the organic layer is washed with water, and dried over magnesium sulfate. Thereafter, the solvent is distilled off under reduced pressure to give 16.3 g of oily S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine ethyl ester.

후처리

  1. customprepared
  2. additionis added dropwise to this reaction mixture
  3. stirringAfter stirring for 1 hour at room temperature
  4. customthe reaction liquid
  5. concentrationis concentrated under reduced pressure
  6. additionTo the resulting residue, ice-cold water is added
  7. extractionAfter extracting with ether
  8. washthe organic layer is washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationThereafter, the solvent is distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-c92e75a3332149228b45d799ac941ab9
출처 데이터셋
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04882326

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