Ethyl 4-(bromomethyl)benzoate → HCID 59383133, compound

HRID 555691Notes

Reaction equation

HRID 555691 reaction equation
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)([OH:3])=[O:2].[CH2:24]([O:26][C:27]([C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1)=[O:28])[CH3:25]>>[CH2:24]([O:26][C:27]([C:29]1[CH:30]=[CH:31][C:32]([CH2:33][O:2][C:1]([C:4]23[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]4[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]4[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]2)[CH2:6][CH2:5]3)=[O:3])=[CH:35][CH:36]=1)=[O:28])[CH3:25]

Participants

3

Reactant 2

HCID 954261Ethyl 4-(bromomethyl)benzoateHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 59383133HCID 59383133, compoundYield 71.5%

Procedure

In a similar manner to Example 8, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (32.3 mg) and 4-ethoxycarbonylbenzyl bromide (28.1 mg) were used to obtain (2S,4S)-1-[[N-[4-(4-ethoxycarbonylbenzyl)oxycarbonyl bicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (34.7 mg).

Sources & evidence

ORD record
ord-bd7ee6ee954145f481c1399dc9f7fa00
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

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