4-Methylmorpholine → HCID 86701299, compound

HRID 1627034Notes

Reaction equation

HRID 1627034 reaction equation
[NH2:1][C@H:2]1[CH2:10][O:9][CH2:8][C@H:7]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C@@H:6]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C@H:5]([CH3:21])[O:4][C:3]1=[O:22].[OH:23][C:24]1[C:25]([C:32](O)=[O:33])=[N:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C(Cl)Cl>[CH2:12]([O:11][C@@H:7]1[C@@H:6]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C@H:5]([CH3:21])[O:4][C:3](=[O:22])[C@@H:2]([NH:1][C:32](=[O:33])[C:25]2[C:24]([OH:23])=[C:29]([O:30][CH3:31])[CH:28]=[CH:27][N:26]=2)[CH2:10][O:9][CH2:8]1)[CH:13]([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110411213-Hydroxy-4-methoxypyridine-2-carboxylic acidHCID 86701298HCID 86701298, compound

Product 1

HCID 86701299HCID 86701299, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (3S,7S,8S,9S)-3-amino-7,8-diisobutoxy-9-methyl-1,5-dioxonan-2-one (170 mg, 0.536 mmol), 3-hydroxy-4-methoxypicolinic acid (136 mg, 0.803 mmol) and HATU (336 mg, 0.857 mmol) in a vial was added CH2Cl2 (3 mL), followed by 4-methylmorpholine (0.353 mL, 3.21 mmol), and the resulting suspension was stirred at room temperature for 3 h. The resulting orange solution was directly purified by flash chromatography (SiO2) to afford the title compound as a white solid (176 mg, 70%): 1H NMR (400 MHz, CDCl3) δ11.95 (s, 1H), 8.68 (d, J=8.0 Hz, 1H), 8.00 (d, J=5.2 Hz, 1H), 6.87 (d, J=5.2 Hz, 1H), 5.10-5.00 (m, 1H), 4.97 (dt, J=12.6, 6.3 Hz, 1H), 4.10-4.01 (m, 1H), 3.94 (s, 3H), 3.87-3.78 (m, 2H), 3.71 (dd, J=8.4, 6.1 Hz, 1H), 3.66-3.57 (m, 1H), 3.38-3.28 (m, 2H), 3.28-3.17 (m, 3H), 1.90-1.76 (m, 2H), 1.45 (t, J=5.8 Hz, 3H), 0.98-0.88 (m, 12H); 13C NMR (101 MHz, CDCl3) δ 170.33, 168.95, 155.38, 148.76, 140.66, 130.23, 109.58, 84.84, 83.75, 80.60, 77.74, 75.32, 73.97, 73.23, 56.11, 52.19, 29.13, 28.89, 19.60, 19.48, 19.47, 19.39, 18.66; ESIMS m/z 469.4 ([M+H]+).

Workup

  1. customThe resulting orange solution was directly purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-59a11e24376342c7b01af149616cea65
Source dataset
uspto-grants-2014_07
Patent number
US08785479B2

Reaction notes

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