Sodium Carbonate → HCID 71204753, compound

HRID 2273109Notes

Reaction equation

HRID 2273109 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C@H:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)[CH3:11])=[O:8]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 12099m-Xylyl bromideHCID 71204683HCID 71204683, compound

Product 1

HCID 71204753HCID 71204753, compoundYield 71.6%

Procedure

The title compound (D24) (48 mg) was prepared according to the general procedure for substituted benzyl amines preparation starting from methyl 4-((S)-1-((R)-piperidine-2-carboxamido)ethyl)benzoate (D12) (50 mg, 0.17 mmol) and 3-methylbenzyl bromide (0.046 ml, 0.34 mmol). (Na2CO3: 2.5 eq; reaction time: 3 hrs; 60° C.)

Sources & evidence

ORD record
ord-7f2b1bdbb24e4dfb829f84e8f4cca7c6
Source dataset
uspto-grants-2015_09
Patent number
US09120824B2

Reaction notes

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