Potassium Carbonate → HCID 56601389, compound

HRID 406165Notes

Reaction equation

HRID 406165 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([O:19][C@H:20]2[C@@H:25]([O:26][CH3:27])[C@@H:24]([NH:28][C:29]3[C:46](=[O:47])[C:45]4[CH:44]=[C:43]5[C:34]([C:35](=[O:63])[C@@:36]6([O:61][CH3:62])[C@@:41]([OH:49])([C:42]5=[O:48])[C:40]5[C:50]([OH:59])=[C:51]([C:55]([O:57][CH3:58])=[O:56])[C:52]([CH3:54])=[CH:53][C:39]=5[CH2:38][C@H:37]6[OH:60])=[C:33]([OH:64])[C:32]=4[C:31](=[O:65])[CH:30]=3)[O:23][C@@H:22]([CH3:66])[C@@H:21]2[O:67][CH3:68])[O:7][C@@H:6]1[CH2:69][O:70]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:27][O:26][C@@H:25]1[C@H:20]([O:19][C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:69][OH:70])[O:7]2)[C@@H:21]([O:67][CH3:68])[C@H:22]([CH3:66])[O:23][C@@H:24]1[NH:28][C:29]1[C:46](=[O:47])[C:45]2[CH:44]=[C:43]3[C:34]([C:35](=[O:63])[C@@:36]4([O:61][CH3:62])[C@@:41]([OH:49])([C:42]3=[O:48])[C:40]3[C:50]([OH:59])=[C:51]([C:55]([O:57][CH3:58])=[O:56])[C:52]([CH3:54])=[CH:53][C:39]=3[CH2:38][C@H:37]4[OH:60])=[C:33]([OH:64])[C:32]=2[C:31](=[O:65])[CH:30]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86660841HCID 86660841, compound

Product 1

HCID 56601389HCID 56601389, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((2S,3S,4R,5R,6S)-3,5-dimethoxy-2-methyl-6-((6R,6aS,14aR)-1,6,8,14a-tetrahydroxy-6a-methoxy-2-(methoxycarbonyl)-3-methyl-7,9,12,14-tetraoxo-5,6,6a,7,9,12,14,14a-octahydrobenzo[a]tetracen-11-ylamino)tetrahydro-2H-pyran-4-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (44 mg, 0.043 mmol) and potassium carbonate (24 mg, 0.17 mmol) in methanol (4 mL) was stirred at room temperature under nitrogen for 4 h. The reaction mixture was concentrated under reduced pressure. The crude product was purified by semi-preparative HPLC (20:80 acetonitrile/water to 60:40 acetonitrile/water with 0.05% TFA over 30 min) to afford (6R,6aS,14aR)-methyl 11-((2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-ylamino)-1,6,8,14a-tetrahydroxy-6a-methoxy-3-methyl-7,9,12,14-tetraoxo-5,6,6a,7,9,12,14,14a-octahydrobenzo[a]tetracene-2-carboxylate (18 mg, 49%) as an orange-red solid: 1H NMR (500 MHz, CD3OD) δ 8.09 (s, 1H), 6.61 (s, 1H), 5.94 (s, 1H), 4.92 (s, 1H), 4.52 (d, J=8.0 Hz, 1H), 3.96-3.85 (m, 3H), 3.79 (s, 3H), 3.75 (s, 3H), 3.65-3.61 (m, 2H), 3.60 (s, 3H), 3.55-3.36 (m, 3H), 3.35 (s, 3H), 3.22-3.15 (m, 5H), 2.38 (s, 3H), 1.25 (d, J=6.0 Hz, 3H); MS (ESI+) m/z 860 (M+H); HPLC 97.6% (AUC), tR 10.95 min.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe crude product was purified by semi-preparative HPLC (20:80 acetonitrile/water to 60:40 acetonitrile/water with 0.05% TFA over 30 min)

Sources & evidence

ORD record
ord-325210917e784e81b58aae64c1008941
Source dataset
uspto-grants-2014_06
Patent number
US08754054B2

Reaction notes

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