Acetic Acid → HCID 135405285、化合物

HRID 989425ノート

反応式

HRID 989425 の反応式
[CH2:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@:10]1([CH2:32][O:33]C(=O)C1C=CC=CC=1)[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:21](=[O:25])[NH:20][C:19]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[N:18][C:17]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C>C(O)C.N1C=CC=CC=1>[CH2:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:32][OH:33])[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:21](=[O:25])[NH:20][C:19]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])=[N:18][C:17]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 136342358HCID 136342358、化合物

生成物 1

HCID 135405285HCID 135405285、化合物収率 87%

試薬・触媒・溶媒 1

HCID 21975839Pyridine ethanol溶媒

実験手順

To a solution of compound 14 (8.2 g, 14.7 mmol) in ethanol/pyridine (8:1, 450 mL) was added 2 M aqueous solution of NaOH (15.5 mL) and the mixture was stirred for 30 min at ambient temperature. Acetic acid (25 mL) was added to the reaction mixture and the solvents were removed under reduced pressure. The residue was crystallised from 20% aqueous ethanol to give 5.8 g (87%) of compound 15 as a white solid material. δH (DMSO-d6) 8.05 (1H, s, 8-H), 7.33-7.26 (5H, m, Bn), 5.85 (1H, s, 1′-H), 5.17 (1H, t, J 5.4, 5′-OH), 4.69 (1H, s, 2′-H), 4.64 (2H, s, Bn), 4.23 (1H, s, 3′-H), 3.95 (1H, d, J 7.9, 1″-H), 3.83 (2H, m, 5′-H), 3.80 (1H, d, J 8.0, 1″-H), 2.78 (1H, m, CHCO), 1.12 (6H, m, CH3). δC (CDCl3) 180.2 (CHCO), 154.8, 148.2, 147.7 (guanine), 137.9, 136.3, (guanine, Bn), 128.3, 127.6, 127.5 (Bn), 120.5 (guanine), 88.2, 85.2, 76.9, 72.1, 71.3, 56.7 (ribose, Bn), 34.8 (CHCO), 18.9 (CH3CH).

後処理

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was crystallised from 20% aqueous ethanol

出典と根拠

ORDレコード
ord-768266d8b43c4127816774bbbc0824f3
出典データセット
uspto-grants-2003_10
特許番号
US06639059B1

反応ノート

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