Triphenylphosphine → Dibenzyl azodicarboxylate

HRID 1097652노트

반응식

HRID 1097652 반응식
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]2[N:33]=[C:32]([CH2:34][CH2:35][CH2:36]O)[O:31][N:30]=2)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:57]1[CH:62]=[CH:61][C:60]([CH2:63][O:64][C:65](/[N:67]=[N:68]/[C:69]([O:71][CH2:72][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)=[O:70])=[O:66])=[CH:59][CH:58]=1>C1COCC1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH2:36][CH2:35][CH2:34][C:32]3[O:31][N:30]=[C:29]([CH2:28][C:25]4[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][CH:26]=4)[N:33]=3)[C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[CH:76]1[CH:75]=[CH:74][C:73]([CH2:72][O:71][C:69](/[N:68]=[N:67]/[C:65]([O:64][CH2:63][C:60]2[CH:61]=[CH:62][CH:57]=[CH:58][CH:59]=2)=[O:66])=[O:70])=[CH:78][CH:77]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dioneHCID 668129393-{3-[(4-Chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}-1-propanol

생성물 2

HCID 5387121Dibenzyl azodicarboxylate수율 177.5%HCID 593955258-Chloro-1-(3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.10 g, 0.34 mmol), 3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}-1-propanol (0.086 g, 0.34 mmol) and triphenylphosphine (0.186 g, 0.69 mmol) in THF (5 ml) was added dibenzylazodicarboxylate (0.204 g, 0.68 mmol) and the solution stirred for 18 h. The solution was then concentrated and the residues chromatographed over silica (20 g, SPE) eluting with DCM initially then DCM/Et2O mixtures to yield the title compound contaminated with dibenzylazodicarboxylate by-products (0.18 g). Material used crude in deprotection step.

후처리

  1. concentrationThe solution was then concentrated
  2. customthe residues chromatographed over silica (20 g, SPE)
  3. washeluting with DCM initially

출처 및 근거

ORD 기록
ord-981292021ff24f748c5004279100e538
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143264B2

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