1,2-Dichloroethane → HCID 59354798, compound

HRID 1776264Notes

Reaction equation

HRID 1776264 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=1.[CH3:23]CN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:46][C:47]([CH3:52])([CH3:51])[C:48]([O-:50])=[O:49]>C(Cl)Cl.O>[CH3:51][C:47]([NH:46][C:20](=[O:22])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:14][CH:15]=1)([CH3:52])[C:48]([O:50][CH3:23])=[O:49]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acidHCID 22316286HCID 22316286, compound

Product 1

HCID 59354798HCID 59354798, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (5.0 g, 0.017 mol) in DCM (50 mL) were added DIPEA (6.6 g, 0.05 mol), HOBT (3.4 g, 0.02 mol) and EDC (4.9 g, 0.02 mol) at RT under an inert atmosphere. After 10 minutes, 2-amino-2-methylpropanoate (3.9 g, 0.02 mol) was added to the reaction mixture and stirring was continued for 4 h. The reaction mixture was diluted with water and extracted with DCM (2×200 mL). The combined organic layers were washed with water and brine, and then dried over Na2SO4. Evaporation of organic solvents in vacuo afforded methyl 2-methyl-2-(2-(4-(quinolin-2-ylmethoxy)phenyl)acetamido)propanoate (5.0 g, 74%) as a white solid.

Workup

  1. waitwas continued for 4 h
  2. extractionextracted with DCM (2×200 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of organic solvents in vacuo

Sources & evidence

ORD record
ord-a63cd526bd134849b16039cddb903506
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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