1,2-Dichloroethane → HCID 178473394, compound

HRID 1185445Notes

Reaction equation

HRID 1185445 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C@@H:28]([NH2:37])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:23][CH2:22]1)=[O:20])[CH3:17].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:16]([O:18][C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C@@H:28]([NH:37][C:13]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=3)[N:5]=2)=[O:15])[CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:25][CH2:26]1)=[O:20])[CH3:17]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 668549254-((S)-2-amino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl esterHCID 178418698HCID 178418698, compound

Product 1

HCID 178473394HCID 178473394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4 g of 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid and 6.4 g of 4-((S)-2-Amino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester in 37 ml of DMF, 3.0 g of HOBT and 3.7 g of EDC was added and the reaction mixture was stirred for 2 h at RT. Then, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by crystallization from ethyl acetate/heptane. Yield: 5.4 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by crystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-f0451891e3614fa9b98aa42b8184341d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

Loading…