Triphenylphosphine → Ethyl 3-{4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylphenyl}-5-isoxazolecarboxylate

HRID 393273Notes

Reaction equation

CCOC(/N=N/C(OCC)=O)=O.[CH2:13]([N:15]1[C:21]2[N:22]=[CH:23][C:24]([CH2:26][CH2:27][OH:28])=[CH:25][C:20]=2[C:19](=[O:29])[N:18]([CH3:30])[C:17]2[CH:31]=[CH:32][CH:33]=[N:34][C:16]1=2)[CH3:14].O[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:46]=[C:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[O:44][N:43]=2)=[CH:38][C:37]=1[CH3:52].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH2:13]([N:15]1[C:21]2[N:22]=[CH:23][C:24]([CH2:26][CH2:27][O:28][C:36]3[CH:41]=[CH:40][C:39]([C:42]4[CH:46]=[C:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[O:44][N:43]=4)=[CH:38][C:37]=3[CH3:52])=[CH:25][C:20]=2[C:19](=[O:29])[N:18]([CH3:30])[C:17]2[CH:31]=[CH:32][CH:33]=[N:34][C:16]1=2)[CH3:14]

Participants

Conditions

Temperature: 25 °C

Procedure

DEAD (55 μL, 0.35 mmol) was added over 30 min to a solution of 11-ethyl-5,11-dihydro-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (70.0 mg, 0.23 mmol), ethyl 3-(4-hydroxy-3-methylphenyl)-5-isoxazolecarboxylate (86.5 mg, 0.35 mmol) and PPh3 (91.8 mg, 0.35 mmol) in THF (2 mL) at 25° C. The reaction mixture was stirred at 25° C. for 18 h. The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2:EtOAc, 10:1) to give the title compound (55 mg, 45% yield).

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by flash chromatography (CH2Cl2:EtOAc, 10:1)

Sources & evidence

ORD record: ord-c6d40716c55c4518a4c6d8a692d56e41
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806265B2

Reaction notes

Loading…