Triethylamine → (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolan-3-yl acetate

HRID 895100

반응식

HRID 895100 반응식
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([I:29])=[N:23][C:24]=2Cl)(=[O:3])[CH3:2].Cl.[CH3:31][O:32][NH2:33].C(N(CC)CC)C>O1CCCC1>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([I:29])=[N:23][C:24]=2[NH:33][O:32][CH3:31])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl esterHCID 521874O-Methylhydroxylamine hydrochloride

생성물 1

HCID 16115476(2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolan-3-yl acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(6-chloro-2-iodopurin-9-yl)oxolan-3-yl acetate (3.71 mmol) in dry tetrahydrofuran (60ml) was mixed with O-methyl hydroxylamine hydrochloride (37.1 mmol) and triethylamine (6.2 mL). The mixture was stirred at room temperature for 96 hours under an atmosphere of nitrogen. The solvent was removed in vacuo and the residue chromatographed on a flash silica gel column eluting with CHCl3—CH3OH (99:1), to give (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-iodo-6-(methoxyamino)purin-9-yl]oxolan-3-yl acetate, a compound of formula (4), which was crystallized from a mixture of chloroform/hexanes (1:1).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed on a flash silica gel column
  3. washeluting with CHCl3—CH3OH (99:1)

출처 및 근거

ORD 기록
ord-d76a1ab68d464322a4e5d1900c8389ca
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06914053B2

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