HCID 136351079, compound → HCID 136195916, compound

HRID 2361729Notes

Reaction equation

HRID 2361729 reaction equation
CO[N:3](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:4]1[NH:5][C:6](=[O:30])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:15]([O:16]C4CCCCO4)[C@@:14]3([C:28]#[CH:29])[F:27])[C:11]=2[N:12]=1>CC(O)=O.C1COCC1.O>[C:28]([C@@:14]1([F:27])[C@H:15]([OH:16])[C@@H:23]([CH2:25][OH:26])[O:24][C@H:13]1[N:10]1[CH:9]=[N:8][C:7]2[C:6](=[O:30])[NH:5][C:4]([NH2:3])=[N:12][C:11]1=2)#[CH:29]

Participants

3

Reactant 1

HCID 136351079HCID 136351079, compound

Product 1

HCID 136195916HCID 136195916, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

20 was synthesized from 19 (0.09 mmol), as described for 9k. The crude material was then stirred at room temperature in AcOH/THF/H2O (4/2/1) solution overnight. The reaction mixture was concentrated under reduced pressure and purified by silica gel chromatography (DCM/MeOH) to yield the title compound. White lyophilized powder. Molecular Formula C26H37FN5O9PS2 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 1.16 (s, 20H), 3.06-3.09 (m, 4H), 3.90-3.91 (d, J=5.40 Hz, 1H), 3.99-4.10 (q, J=6.70 Hz and J=7.00 Hz, 4H), 4.32-4.38 (m, 2H), 4.63 (m, 1H), 6.10-6.14 (d, J=16.93 Hz, 1H), 6.69 (s, 2H), 7.79 (s, 1H), 10.96 (s, 1H) 31P NMR (DMSO-d6, 162 MHz) δ (ppm) −1.91 (s, 1P) 19F NMR (DMSO-d6, 376 MHz) δ (ppm) −156.82 (s, 1F) Scan ES+ 678 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-be21f810c17d47a5884a1d927bf6ce08
Source dataset
uspto-grants-2014_04
Patent number
US08691788B2

Reaction notes

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