Sodium Carbonate → HCID 71204721, compound

HRID 2273118Notes

Reaction equation

HRID 2273118 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([NH:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10])=[O:7].[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][N:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([NH:8][C@H:9]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)[CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 12099m-Xylyl bromideHCID 71204726HCID 71204726, compound

Product 1

HCID 71204721HCID 71204721, compoundYield 43.8%

Procedure

The title compound (D33) (30 mg) was prepared according to the general procedure for substituted benzyl amines preparation starting from methyl 4-((S)-1-((R)-pyrrolidine-2-carboxamido)ethyl)benzoate (D14) (50 mg, 0.18 mmol) and 3-methylbenzyl bromide (0.05 ml, 0.36 mmol). (Na2CO3: 2.5 eq; reaction time: 5 hrs; 70° C.)

Sources & evidence

ORD record
ord-93b56cbeb5c9441682a90b433f24bd43
Source dataset
uspto-grants-2015_09
Patent number
US09120824B2

Reaction notes

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