Benzenesulfonyl chloride → N-{[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6(phenethylamino)-9H-purin-2-yl]methyl}benzenesulfonamide

HRID 2268395ノート

反応式

HRID 2268395 の反応式
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][CH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@H:22]2[C@H:26]([OH:27])[C@H:25]([OH:28])[C@@H:24]([CH2:29][O:30][CH3:31])[O:23]2)=[C:15]([NH:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:14]=1.C(N(CC)CC)C>O1CCCC1>[OH:27][C@@H:26]1[C@H:25]([OH:28])[C@@H:24]([CH2:29][O:30][CH3:31])[O:23][C@H:22]1[N:19]1[CH:18]=[N:17][C:16]2[C:20]1=[N:21][C:13]([CH2:12][NH:11][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])=[N:14][C:15]=2[NH:32][CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 59975306(2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

生成物 1

HCID 20709174N-{[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6(phenethylamino)-9H-purin-2-yl]methyl}benzenesulfonamide収率 98.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Phenylsulfonylchloride (57 mg, 0.33 mmol) was added to a stirred solution of (2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol (150 mg, 0.36 mmol) (preparation 48) and triethylamine (110 mg, 1.08 mmol) in tetrahydrofuran (24 ml). The reaction mixture was stirred for 30 min at room temperature and then the solvent was removed under reduced pressure. The residue was azeotroped with dichloromethane and then purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5) to give the title compound (180 mg) as a foam. MS: 577 (MNa+).

後処理

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was azeotroped with dichloromethane
  3. custompurified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5)

出典と根拠

ORDレコード
ord-c0821e47015f4d54aff7773c23dbc1d1
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

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