alpha-Bromo-o-fluorotoluene → HCID 59468959, compound

HRID 1690090Notes

Reaction equation

[NH2:1][C:2]([C@:4]1([CH3:23])[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[N:5]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:3].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>>[NH2:1][C:2]([C@@:4]1([CH3:23])[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:27][C:26]3[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=3[F:24])=[CH:11][CH:10]=2)[N:5]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:3]

Participants

Reactant 2

HCID 67968alpha-Bromo-o-fluorotoluene

HCID 59468953HCID 59468953, compound

Product 1

HCID 59468959HCID 59468959, compound

Procedure

The title compound was prepared (80 mg) using a similar procedure as set out earlier in Description 11 starting from 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-2-methyl-1-pyrrolidinecarboxylate (D22, 55 mg, 0.17 mmol)) and 2-fluorobenzyl bromide; Rt (HPLC): 5.87 min; MS: (ES/+) 451 m/z: [M+Na+]; C24H29FN2O4 requires 428.

Sources & evidence

ORD record: ord-06acdbf0840640e5b2706cdcef0e7ea1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153623B2

Reaction notes

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