Diisopropylethylamine → Acetic acid ((1S,2R,3S,4R)-4-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentylcarbamoyl)-methyl ester

HRID 1882542

反応式

HRID 1882542 の反応式
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])=[O:18])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[C:4](Cl)[N:3]=1.[NH2:27][CH2:28][CH:29]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[OH:36][C:33]1[CH:34]=[CH:35][C:30]([CH:29]([C:37]2[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=2)[CH2:28][NH:27][C:4]2[N:3]=[C:2]([Cl:1])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])=[O:18])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[CH:31][CH:32]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 217102804,4'-(2-Aminoethylidene)bisphenolHCID 59419014Acetic acid [(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl-carbamoyl]-methyl ester

生成物 1

HCID 86647545Acetic acid ((1S,2R,3S,4R)-4-{6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-2-chloro-purin-9-yl}-2,3-dihydroxy-cyclopentylcarbamoyl)-methyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

Acetic acid [(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl-carbamoyl]-methyl ester (Intermediate ZJ; 1 equivalent) and 4,4′-(2-aminoethylidene)bis-phenol (1.1 equivalents; prepared as described by Schelkun, R. M. et al. Bioorg. Med. Chem. Lett. (1999), 9(16), pp 2447-2452) are combined in dry THF and treated with DIPEA (1.2 equivalents) and stirred at 50° C. overnight. The reaction is diluted with ethyl acetate and washed consecutively with water (×2) and brine, before drying over magnesium sulfate, filtering and removal of the volatile components under reduced pressure to afford the title compound.

後処理

  1. washwashed consecutively with water (×2) and brine
  2. dry with materialbefore drying over magnesium sulfate
  3. filtrationfiltering
  4. customremoval of the volatile components under reduced pressure

出典と根拠

ORDレコード
ord-1c7e9dc2a717416db4e19c2acfa2aa92
出典データセット
uspto-grants-2012_11
特許番号
US08318750B2

関連ノート

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