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Benzyl chloroformate → HCID 86658527, 화합물

HRID 537080
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HRID 537080 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[O:10][CH2:11][C@@H:12]2[C@@H:16]([OH:17])[C@:15]([F:19])([CH3:18])[C@H:14]([N:20]3[CH:28]=[N:27][C:26]4[C:21]3=[N:22][C:23]([NH:31][C:32]([C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:24][C:25]=4[O:29][CH3:30])[O:13]2)=[CH:5][CH:4]=1.[CH:69]1[CH:74]=[CH:73][C:72]([CH2:75][O:76][C:77](Cl)=[O:78])=[CH:71][CH:70]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:77](=[O:78])([O:17][C@H:16]1[C@:15]([F:19])([CH3:18])[C@H:14]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][C:23]([NH:31][C:32]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:24][C:25]=3[O:29][CH3:30])[O:13][C@@H:12]1[CH2:11][O:10][C:9]([C:61]1[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=1)([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[O:76][CH2:75][C:72]1[CH:73]=[CH:74][CH:69]=[CH:70][CH:71]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86658528HCID 86658528, 화합물

생성물 1

HCID 86658527HCID 86658527, 화합물수율 94.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

반응 조건

온도
0 °C

실험 절차

To a solution of nucleoside 114 (2.52 g, 2.75 mmol) in anhydrous DCM (8 mL) was added DMAP (1.01 g, 8.2 mmol) and the solution was cooled at 0° C. in an ice-water bath. Cbz-Cl (0.77 g, 4.2 mmol) was added via a syringe to the mixture and resulted in a cloudy reaction mixture. The mixture was stirred at room temperature for 24 hours and sat. NaHCO3 (10 mL) was added. The mixture was partitioned in DCM and water. The organic layer was dried over Na2SO4 and concentrated to a white foam solid. The residue was purified via column chromatography (1060% EtOAc in hexanes) to afford 2.74 g product, 115, as a white foam solid (yield, 95%).

후처리

  1. customresulted in a cloudy reaction mixture
  2. customThe mixture was partitioned in DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to a white foam solid
  5. customThe residue was purified via column chromatography (1060% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-f1005d26ef4843d6879fa2c71ab86179
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859756B2

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