Acetic Acid → HCID 135405285, compound

HRID 989425Notes

Reaction equation

HRID 989425 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 135405285HCID 135405285, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-768266d8b43c4127816774bbbc0824f3
Source dataset
uspto-grants-2003_10
Patent number
US06639059B1

Reaction notes

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