1,2-Dichloroethane → HCID 178501467, compound

HRID 1185481Notes

Reaction equation

HRID 1185481 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.Cl.[CH3:16][O:17][C:18](=[O:30])[C@@H:19]([NH2:29])[CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH3:16][O:17][C:18](=[O:30])[C@@H:19]([NH:29][C:12]([C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:14])[CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 16218751L-Glutamic acid, 5-(1,1-dimethylethyl) 1-methyl ester, hydrochloride (1:1)HCID 178418933HCID 178418933, compound

Product 1

HCID 178501467HCID 178501467, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5 g 4-Hydroxy-quinoline-2-carboxylic acid and 5 g of (S)-2-Amino-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride in 50 ml of DMF, 4.0 g of HOBT, 5.1 g of EDC and 6 g of NEM was added and the reaction mixture was stirred for 16 h at RT. Then, the reaction mixture was diluted with water and extracted with DCM. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by re-crystallisation from ethyl acetate and dried under reduced pressure. Yield: 6.5 g.

Workup

  1. extractionextracted with DCM
  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 re-crystallisation from ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b93da7ca845f437781afa6758bf24f67
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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