Acetic Acid → HCID 135405285, 화합물

HRID 989425노트

반응식

HRID 989425 반응식
[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

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 136342358HCID 136342358, 화합물

생성물 1

HCID 135405285HCID 135405285, 화합물수율 87%

시약·촉매·용매 1

HCID 21975839Pyridine ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-768266d8b43c4127816774bbbc0824f3
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06639059B1

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