Triethylamine → cis-2',3',5'-tri-O-benzoyl-2-chloro-N-(2-phenoxycyclopentyl)adenosine

HRID 1379636노트

반응식

HRID 1379636 반응식
[O:1]([C@H:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:22][C@@H:23]1[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:25][C@H:24]1[N:47]1[CH:55]=[N:54][C:53]2[C:48]1=[N:49][C:50]([Cl:57])=[N:51][C:52]=2Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCOCC1>[C:14]([O:22][C@@H:23]1[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:26]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:25][C@H:24]1[N:47]1[C:48]2[N:49]=[C:50]([Cl:57])[N:51]=[C:52]([NH:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][C@@H:8]3[O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:53]=2[N:54]=[CH:55]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 30815077rac-(1R,2S)-2-phenoxycyclopentan-1-amine

생성물 1

HCID 22877238cis-2',3',5'-tri-O-benzoyl-2-chloro-N-(2-phenoxycyclopentyl)adenosine수율 94.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

cis-2-Phenoxycyclopentylamine (0.75 g, 4.23 mmol) was combined with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.95 g, 4.7 mmol) and triethylamine (0.64 g, 6.3 mmol) in dioxan (30 ml) and stirred for 50 h. The reaction mixture was filtered, evaporated and the residue dissolved in ethyl acetate and washed with water (2×50 ml). The organic phase was dried (MgSO4), evaporated and the residue coevaporated to give cis-2',3',5'-tri-O-benzoyl-2-chloro- N-(2-phenoxycyclopentyl)adenosine (3.1 g, 90%) as an amorphous foam, which was deprotected using saturated methanolic ammonia (50 ml). After 70 h at room temperature the reaction mixture was evaporated and the residue purified by flash chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (19:1). The title cis-2-chloro- N-(2-phenoxycyclopentyl)adenosine (0.925 g, 53%) was obtained as an amorphous foam (a 1:1 mixture of diastereoisomers), 1H NMR (DMSO-d6)δ 1.58-2.15 (6H, 3m, --CH2CH2CH2 --), 3.51-3.60 (1 H, m, H-5'a), 3.62-3.71 (1H, m, H-5'b), 3.95 (1H, br q, H-4'), 4.12 (1H, br q, H-3'), 4.46-4.62 (2H, m, H-2' and --CH), 4.82-4.89 (1H, m, --CH), 5.07 (1H, br t, 5'-OH), 5.22, 5.49 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 6.80-6.91 (3H, m, Ar--H), 7.15-7.24 (2H, t, Ar--H), 7.99, 8.22 (1H, d & m, N--H), 8.41, 8.45 (1 H, 2s, H-8).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water (2×50 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-f1ea27ca49c948ffa185f839c5b9280f
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05672588

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