Phthalimide → HCID 69420144, 화합물

HRID 1374072

반응식

HRID 1374072 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[C:31]([NH:39][C:40]1[C:41]2[N:42]=[CH:43][N:44]([C:53]=2[N:54]=[CH:55][N:56]=1)[C@@H:45]1[O:52][C@H:49]([CH2:50][OH:51])[C@@H:47]([OH:48])[CH2:46]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:20]1(=[O:30])[N:24]([CH:50]([OH:51])[C@H:49]2[O:52][C@@H:45]([N:44]3[C:53]4[N:54]=[CH:55][N:56]=[C:40]([NH:39][C:31](=[O:38])[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[C:41]=4[N:42]=[CH:43]3)[CH2:46][C@@H:47]2[OH:48])[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 107558N-benzoyl-2'-deoxyadenosine

생성물 1

HCID 69420144HCID 69420144, 화합물수율 29.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

13.11 g (50 mmol) triphenylphosphine, 6.99 g (47.5 mmol) phthalimide and 17.77 g (50 mmol) N6-benzoyl-2′-deoxyadenosine were stirred in 400 mL dry THF, and added 9.84 mL (50 mmol) of diisopropyl azodicarboxylate under a nitrogen atmosphere. After stirring in an ice-water bath for 2 h and at the ambient temperature for 4 h, the reaction mixture was concentrated and the residue was added 100 mL dichloromethane. The precipitates thus formed were removed by filtration and the filtrate was concentrated and flashed through a silica gel column with 2:1 dichloromethane-THF and 19:1 dichloromethane-methanol to give 7.1 g of 5′-phthalimido-N6-benzoyl-2′-deoxyadenosine.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue was added 100 mL dichloromethane
  3. customThe precipitates thus
  4. customformed
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-f641fc51dfce4851aeafac4cc703fe78
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07164014B2

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