2-Fluorobenzonitrile → HCID 59468930, compound

HRID 1717182Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C@:10]3([CH2:16][CH2:15][NH:14][C:13]3=[O:17])[N:9]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:4][CH:3]=1.F[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[C:28]#[N:29]>>[C:28]([C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C@:10]3([CH2:16][CH2:15][NH:14][C:13]3=[O:17])[N:9]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:4][CH:3]=1)#[N:29]

Participants

Reactant 2

HCID 678552-Fluorobenzonitrile

HCID 59468973HCID 59468973, compound

Product 1

HCID 59468930HCID 59468930, compoundYield 66%

Procedure

1,1-Dimethylethyl (2R,5R)-2-{4-[(2-cyanophenyl)oxy]phenyl}-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D28, 58 mg, 66%) was synthesized using a similar procedure as set out earlier in Description 13 using 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-2-methyl-1-pyrrolidinecarboxylate (D25, 66 mg, 0.198 mmol) and 2-fluoro-benzonitrile; Rt (HPLC): 5.34 min; MS: (ES/+) m/z: 456 [M+Na+]; C25H27N3O4 requires 433.

Sources & evidence

ORD record: ord-ca3468ae16b344a28866e3417fa713ca
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803833B2

Reaction notes

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