Triphenylphosphine → Methyl 3'-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-[1,1'-biphenyl]-4-carboxylate

HRID 393289Notes

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:37]=[C:38]([C:42]2[CH:47]=[CH:46][C:45]([C:48]([O:50][CH3:51])=[O:49])=[CH:44][CH:43]=2)[CH:39]=[CH:40][CH:41]=1.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:40]3[CH:39]=[C:38]([C:42]4[CH:47]=[CH:46][C:45]([C:48]([O:50][CH3:51])=[O:49])=[CH:44][CH:43]=4)[CH:37]=[CH:36][CH:41]=3)=[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

A solution of DEAD (84 μL, 0.54 mmol) in THF (0.5 mL) was added over 2 h to an ice-cold 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 (100 mg, 0.34 mmol), methyl 3′-hydroxy-[1,1′-biphenyl]-4-carboxylate (123 mg, 0.54 mmol) and PPh3 (141 mg, 0.54 mmol) in THF (3.4 mL). The reaction mixture was stirred at 25° C. for 12 h then concentrated under reduced pressure. The residue was purified by flash chromatography (toluene:EtOAc, 85:15) to give the title compound (74 mg, 43% yield) as white gummy solid.

Workup

concentrationthen concentrated under reduced pressure
customThe residue was purified by flash chromatography (toluene:EtOAc, 85:15)

Sources & evidence

ORD record: ord-2c474c5e6c8a40f2a57b3561ed3cb86c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806265B2

Reaction notes

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