Diphenylphosphinic chloride → HCID 75986159, compound
Reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]2[NH:15][C:16](=[O:37])[C:17]3([CH:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[CH:20]([C:29](O)=[O:30])[NH:19][CH:18]3[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]2=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:62][C:63]1[CH:70]=[CH:69][C:66]([C:67]#[N:68])=[CH:65][C:64]=1[O:71][CH3:72]>>[C:67]([C:66]1[CH:69]=[CH:70][C:63]([NH:62][C:29]([CH:20]2[NH:19][CH:18]([CH2:32][C:33]([CH3:35])([CH3:36])[CH3:34])[C:17]3([C:12]4[C:13](=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=4)[NH:15][C:16]3=[O:37])[CH:21]2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[O:30])=[C:64]([O:71][CH3:72])[CH:65]=1)#[N:68]Participants
5
Reactant 4
Product 1
Procedure
In a manner similar to the method described in Example 5, rac-(2′S,3′R,4′R,5′R)-6-chloro-4′-(3-chloro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid trifluoroacetic acid prepared in Example 63 (1.0 g, 1.8 mmol), was reacted with diisopropylethylamine (2.1 g, 16.5 mmol), diphenylphosphinic chloride (1.74 g, 7.3 mmol), then reacted with 4-amino-3-methoxy-benzonitrile prepared in Example 57 (0.54 g, 3.7 mmol) to give rac-(2′S,3′R,4′R,5′R)-6-chloro-4′-(3-chloro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid (4-cyano-2-methoxy-phenyl)-amide as a white solid (Yield, 0.17 g, 16%).
Workup
- customto give
Sources & evidence
- ORD record
- ord-7e2edcb9fb0a47118313835070f7c004
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088815B2
Reaction notes
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