2-Methoxyethylamine → HCID 178495866, compound

HRID 406159Notes

Reaction equation

HRID 406159 reaction equation
[OH:1][C:2]1[C:7]2[C@@:8]3([OH:45])[C@@:21]([O:25][CH3:26])([C@H:22]([OH:24])[CH2:23][C:6]=2[CH:5]=[C:4]([CH3:46])[C:3]=1[C:47]([O:49][CH3:50])=[O:48])[C:20](=[O:27])[C:19]1[C:10](=[CH:11][C:12]2[C:13](=[O:43])[C:14]([NH:30][C@@H:31]4[C@H:36]([O:37][CH3:38])[C@H:35]([OH:39])[C@@H:34]([O:40][CH3:41])[C@H:33]([CH3:42])[O:32]4)=[CH:15][C:16](=O)[C:17]=2[C:18]=1[OH:28])[C:9]3=[O:44].[CH3:51][O:52][CH2:53][CH2:54][NH2:55]>CO>[OH:1][C:2]1[C:7]2[C@@:8]3([OH:45])[C@@:21]([O:25][CH3:26])([C@H:22]([OH:24])[CH2:23][C:6]=2[CH:5]=[C:4]([CH3:46])[C:3]=1[C:47]([O:49][CH3:50])=[O:48])[C:20](=[O:27])[C:19]1[C:10](=[CH:11][C:12]2[C:13](=[O:43])[C:14]([NH:30][C@@H:31]4[C@H:36]([O:37][CH3:38])[C@H:35]([OH:39])[C@@H:34]([O:40][CH3:41])[C@H:33]([CH3:42])[O:32]4)=[CH:15]/[C:16](=[N:55]\[CH2:54][CH2:53][O:52][CH3:51])/[C:17]=2[C:18]=1[OH:28])[C:9]3=[O:44]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 67121454(6R,6aS,14aR)-methyl 1,6,8,14a-tetrahydroxy-11-((2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-ylamino)-6a-methoxy-3-methyl-7,9,12,14-tetraoxo-5,6,6a,7,9,12,14,14a-octahydrobenzo[a]tetracene-2-carboxylate

Product 1

HCID 178495866HCID 178495866, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (6R,6aS,14aR)-methyl 1,6,8,14a-tetrahydroxy-11-((2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-ylamino)-6a-methoxy-3-methyl-7,9,12,14-tetraoxo-5,6,6a,7,9,12,14,14a-octahydrobenzo[a]tetracene-2-carboxylate (100 mg, 0.14 mmol) in methanol (3 mL) was added 2-methoxyethanamine (107 mg, 1.43 mmol). The reaction mixture was stirred at room temperature under nitrogen for 3 h. The reaction was quenched by adding saturated ammonium chloride solution (15 mL). Then it was extracted with chloroform (75 mL) and washed with water (2×25 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the crude product. The crude material was purified by preparative TLC (silica gel, 90:10 chloroform/methanol) to afford (6R,6aS,14aR,E)-methyl 1,6,8,14a-tetrahydroxy-11-((2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-ylamino)-6a-methoxy-9-(2-methoxyethylimino)-3-methyl-7,12,14-trioxo-5,6,6a,7,9,12,14,14a-octahydrobenzo[a]tetracene-2-carboxylate (33.8 mg, 31.2%) as a dark blue solid: 1H NMR (500 MHz, CDCl3) δ 11.95 (s, 1H), 7.93 (s, 1H), 6.91 (d, J=8.5 Hz, 1H), 6.49 (s, 1H), 6.05 (s, 1H), 5.27 (s, 1H), 4.99 (t, J=8.0 Hz, 1H), 4.74-4.69 (m, 2H), 3.83 (s, 4H), 3.79 (s, 4H), 3.72-3.69 (m, 4H), 3.65-3.59 (m, 4H), 3.57-3.55 (m, 1H), 3.40 (s, 3H), 3.37 (s, 3H), 3.14 (t, J=9.1 Hz, 1H), 2.48 (d, J=3.8 Hz, 1H), 2.37 (s, 3H), 1.58 (br s, 1H), 1.37 (d, J=6.1 Hz, 3H); MS (ESI+) m/z 755 (M+H); HPLC 88.9% (AUC), tR=11.14 min.

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated ammonium chloride solution (15 mL)
  3. extractionThen it was extracted with chloroform (75 mL)
  4. washwashed with water (2×25 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product
  10. customThe crude material was purified by preparative TLC (silica gel, 90:10 chloroform/methanol)

Sources & evidence

ORD record
ord-3f1fc513dc314f3fbad3dbef07705d0e
Source dataset
uspto-grants-2014_06
Patent number
US08754054B2

Reaction notes

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