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Water → Nalpha-Trityl-S-(9H-xanthen-9-yl)-L-cysteine

HRID 19462
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HRID 19462 반응식
[CH:1]1[C:14]2[CH:13]([S:15][CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O.C(NCC)C.[C:28](Cl)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[C:28]([NH:18][C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][S:15][CH:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8021DiethylamineHCID 10566205S-(9H-Xanthen-9-yl)cysteine

생성물 1

HCID 11214896Nalpha-Trityl-S-(9H-xanthen-9-yl)-L-cysteine수율 78%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
4 °C

실험 절차

A sample of 1.0 g of S-(9H-Xanthen-9-yl)cysteine (3.3 mmole) from Example 4 was dissolved in 10 ml of chloroform. To the solution was added 1.5 ml of water and 1.5 ml of diethylamine. The mixture was cooled to 4° C. by an ice bath and 0.98 g of trityl chloride (3.5 mmole) was added in portions over a period of 30 min. After 2 h of stirring at room temperature. The reaction mixture was separated. The organic phase was washed twice with 4% diethylamine aqueous solution. The organic layer was dried over Na2SO4. The drying reagent was removed by filtration and the filtrate was condensed to dryness by rotary evaporation. The residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol. The resultant diethyl ammonium salt was partitioned between 10 ml of ethyl acetate and 7 ml of 5% aqueous KHSO4 and 7 ml of water. The ethyl acetate layer was separated and was dried over MgSO4 and was concentrated to get 1.4 g of product.

후처리

  1. customThe reaction mixture was separated
  2. washThe organic phase was washed twice with 4% diethylamine aqueous solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe drying reagent was removed by filtration
  5. customcondensed to dryness
  6. customby rotary evaporation
  7. temperatureThe residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol
  8. customThe resultant diethyl ammonium salt was partitioned between 10 ml of ethyl acetate and 7 ml of 5% aqueous KHSO4 and 7 ml of water
  9. customThe ethyl acetate layer was separated
  10. dry with materialwas dried over MgSO4
  11. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-92954937813a4d2a95d4030fa83e8f21
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745392B2

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