1,2-Dichloroethane → HCID 59354798, compound

HRID 655360Notes

Reaction equation

HRID 655360 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-951186a76f23443b883ca0ae90074f61
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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