Benzocaine → HCID 67128324, compound

HRID 2382249Notes

Reaction equation

HRID 2382249 reaction equation
[N:1]1([CH:6]([CH3:10])[C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:35]([O:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)[CH3:36].CCN(C(C)C)C(C)C>CN(C=O)C.O.C(#N)C>[N:1]1([CH:6]([CH3:10])[C:7]([NH:45][C:42]2[CH:41]=[CH:40][C:39]([C:38]([O:37][CH2:35][CH3:36])=[O:46])=[CH:44][CH:43]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 4

HCID 2337BenzocaineHCID 81531DiisopropylethylamineHCID 31571772-(Pyrrolidin-1-yl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67128324HCID 67128324, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To the 2-pyrrolidin-1-yl-propanoic acid (200 mg, 1.4 mmol) in DMF (10 mL), was added HATU (586 mg, 1.5 mmol), 4-amino-benzoic acid ethyl ester (231 mg, 1.4 mmol) and DIPEA (0.5 mL, 2.8 mmol). The reaction mixture was stirred at room temperature for 16 hours, diluted with water and acetonitrile, purified by preparative HPLC, and lyophilized to give ethyl 4-(2-(pyrrolidin-1-yl)propanamido)benzoate.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-eecb134f15ea416d962e28c13b6fa6e6
Source dataset
uspto-grants-2012_09
Patent number
US08258316B2

Reaction notes

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