1,2-Dichloroethane → HCID 178452372, compound

HRID 1185477Notes

Reaction equation

HRID 1185477 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.FC(F)(F)C(O)=O.[CH2:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36](=[O:49])[C@@H:37]([NH2:48])[CH2:38][CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:32][CH2:31]1)=[O:29])[CH2:24][CH2:25][CH3:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:23]([O:27][C:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36](=[O:49])[C@@H:37]([NH:48][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])[CH2:38][CH2:39][O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:34][CH2:35]1)=[O:29])[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 685991994-((S)-2-Amino-4-benzyloxy-butyryl)-piperazine-1-carboxylic acid butyl ester trifluoroacetateHCID 178418698HCID 178418698, compound

Product 1

HCID 178452372HCID 178452372, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g of 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid and 1.8 g of 4-((S)-2-Amino-4-benzyloxy-butyryl)-piperazine-1-carboxylic acid butyl ester trifluoroacetate in 12 ml of DMF, 566 mg of NEM, 1.1 g of HOBT and 1.4 g of EDC was added and the reaction mixture was stirred for 16 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 chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 650 mg.

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 chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-c6a7bea7b0a64b51a822c6aafb348875
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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