1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58271193, compound

HRID 1665249Notes

Reaction equation

HRID 1665249 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)=[C:4]([F:19])[CH:3]=1.Cl.[CH2:21]([O:23][C:24](=[O:28])[CH2:25][NH:26][CH3:27])[CH3:22].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:21]([O:23][C:24](=[O:28])[CH2:25][N:26]([C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([CH2:7][O:6][C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][C:4]=2[F:19])[CH:9]=1)[CH3:27])[CH3:22]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 181649HOAtHCID 28831601HCID 28831601, compound

Product 1

HCID 58271193HCID 58271193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-bromo-2-fluoro-phenoxymethyl)-benzoic acid (5.21 g, 16.02 mmol), N-methyl glycine ethyl ester hydrochloride (4.9 g, 32.05 mmol), DIEA (14 mL, 80.01 mmol), EDCI (6.1 g, 32.05 mmol) and HOAT (4.4 g, 32.05 mmol) in methylene chloride (300 mL) was stirred at room temperature for 12 h. The mixture was evaporated and the residue was purified by column (0-50% EtOAc in hexane) to give {{[3-(4-bromo-2-fluoro-phenoxymethyl)-benzoyl]-methyl-amino}-acetic acid ethyl ester, 4.5 g (66%). LC-MS (ES) calculated for C19H19BrFNO4, 423; found m/z 424 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column (0-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-a5cc695c4be244b4ba26475250f07b70
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

Loading…