Water → 4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one

HRID 20693Notes

Reaction equation

HRID 20693 reaction equation
O.C(N(CC)CC)C.C([O:12][C@H:13]1[C@H:18]([O:19]C(=O)C)[C@@H:17]([O:23]C(=O)C)[C@H:16]([O:27][C:28]2[C:29]([O:48][CH3:49])=[CH:30][CH:31]=[C:32]3[C:37]=2[O:36][C:35](=[O:38])[CH:34]=[C:33]3[NH:39][C:40]2[C:45]([Cl:46])=[CH:44][N:43]=[CH:42][C:41]=2[Cl:47])[O:15][C@@H:14]1[CH2:50][O:51]C(=O)C)(=O)C>CO>[Cl:47][C:41]1[CH:42]=[N:43][CH:44]=[C:45]([Cl:46])[C:40]=1[NH:39][C:33]1[C:32]2[C:37](=[C:28]([O:27][C@H:16]3[C@H:17]([OH:23])[C@@H:18]([OH:19])[C@H:13]([OH:12])[C@@H:14]([CH2:50][OH:51])[O:15]3)[C:29]([O:48][CH3:49])=[CH:30][CH:31]=2)[O:36][C:35](=[O:38])[CH:34]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 24849804(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Product 1

HCID 248492214-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (1.5 mL) and then triethylamine (1.5 mL) were added to a solution of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy-tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.137 g, 0.200 mmol Example 60) and MeOH (1.5 mL). The mixture was stirred at rt overnight, concentrated, and then purified by reverse-phase HPLC (25→100% MeCN/H2O) to give 4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one: 1H NMR (400 MHz, CD3OD): δ 8.72 (s, 2H), 7.88 (d, 1H), 7.20 (d, 1H), 5.17 (d, 1H), 4.77 (s, 1H), 4.01 (s, 3H), 3.76 (dd, 1H), 3.63 (dd, 1H), 3.54 (dd, 1H), 3.43 (m, 2H), 3.25 (m, 1H); MS (ESI): 514.9.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC (25→100% MeCN/H2O)

Sources & evidence

ORD record
ord-dc67f53d5a3a40c4ab6f5f8b2f16119b
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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