2,4,6-Tris(1-methylethyl)benzenesulfonyl chloride → 5-Acetylamino-7-(2,4,6-triisopropyl-benzenesulfonyloxy)-3-(2,3,5-tri-o-acetyl-beta-d-ribofuranosyl)thiazolo[4,5-d]pyrimidin-2-one

HRID 583744

반응식

HRID 583744 반응식
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:33])[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[C:9]=2[N:10]=1)(=[O:3])[CH3:2].[CH:34]([C:37]1[CH:42]=[C:41]([CH:43]([CH3:45])[CH3:44])[CH:40]=[C:39]([CH:46]([CH3:48])[CH3:47])[C:38]=1[S:49](Cl)(=[O:51])=[O:50])([CH3:36])[CH3:35]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH:4][C:5]1[N:6]=[C:7]([O:33][S:49]([C:38]2[C:39]([CH:46]([CH3:47])[CH3:48])=[CH:40][C:41]([CH:43]([CH3:45])[CH3:44])=[CH:42][C:37]=2[CH:34]([CH3:36])[CH3:35])(=[O:51])=[O:50])[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[C:9]=2[N:10]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 135508503HCID 135508503, 화합물

생성물 1

HCID 208186525-Acetylamino-7-(2,4,6-triisopropyl-benzenesulfonyloxy)-3-(2,3,5-tri-o-acetyl-beta-d-ribofuranosyl)thiazolo[4,5-d]pyrimidin-2-one수율 92%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

The intermediate from Step 1 above (500 mg, 0.98 mmol) was dissolved in DCM (15 mL) at ambient temperature. DMAP (7.3 mg, 0.06 mmol), and TEA (16 ml, 11 mmol) were added to the solution, followed by 2,4,6-triisopropylbenzenesulfonyl chloride (454 mg, 1.5 mmol). After 1 h the reaction had gone to completion, the crude mixture was concentrated, and then purified by flash chromatography (SiO2, 10% EtOAc—CHCl3), affording 690 mg (92%) of 5-acetylamino-7-(2,4,6-triisopropyl-benzenesulfonyloxy)-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)thiazolo[4,5-d ]pyrimidin-2-one as a foaming white solid 17: 74.5-76.3° C.; Rf=0.7 (SiO2, 20% EtOAc—CHCl3); 1H (400 MHz, d6-DMSO) δ 10.83 (s, 1H), 7.39 (s, 2H), 6.03 (d, J=4.0, 1H), 5.91-5.96 (m, 1H), 5.69 (t, J=6.4, 1H), 4.30-4.70 (m, 1H), 4.22-4.26 (m, 1H), 4.16-4.20 (m, 1H), 3.90-4.00 (m, 2H), 2.97-3.01 (m, 1H), 2.07 (s, 3H), (s, 3H), 2.04 (s, 3H), 1.88 (s, 3H), 1.17-1.25 (m, 18H).

후처리

  1. concentrationthe crude mixture was concentrated
  2. custompurified by flash chromatography (SiO2, 10% EtOAc—CHCl3)

출처 및 근거

ORD 기록
ord-729c81c78b4540e589b3a8550b545efc
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924271B2

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