Triphenylphosphine → tert-Butyl 2-((2'-cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-yloxy)methyl)morpholine-4-carboxylate
Reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:41][CH:42]1[O:47][CH2:46][CH2:45][N:44]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:43]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:13]=[C:14]([O:16][CH2:41][CH:42]2[O:47][CH2:46][CH2:45][N:44]([C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])[CH2:43]2)[CH:15]=1)#[N:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of methyl 2′-cyano-5-hydroxy-4′-methylbiphenyl-3-carboxylate (150 mg, 0.56 mmol), triphenylphosphine (220 mg, 0.84 mmol), tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (130 mg, 0.62 mmol) (Bioorg. Med. Chem. Lett. 2007, 17, 533) in CH2Cl2 (5 mL) at room temperature under nitrogen was slowly added a solution of diisopropyl azodicarboxylate (340 mg, 1.7 mmol) in CH2Cl2 (3 mL). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound.
Workup
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-cb6b51220b6047c3b309654e813bb10d
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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