1,2-Dichloroethane → 2-[(S)-3-tert-Butoxycarbonyl-1-(4-ethoxycarbonyl-piperazine-1-carbonyl)-propylcarbamoyl]-quinoline-4-carboxylic acid ethyl ester

HRID 1185440Notes

Reaction equation

HRID 1185440 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]([OH:18])=O)[CH:7]=1)=[O:5])[CH3:2].[CH2:19]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30](=[O:42])[C@@H:31]([NH2:41])[CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:26][CH2:25]1)=[O:23])[CH3:20].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16](=[O:18])[NH:41][C@H:31]([C:30]([N:27]2[CH2:28][CH2:29][N:24]([C:22]([O:21][CH2:19][CH3:20])=[O:23])[CH2:25][CH2:26]2)=[O:42])[CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 66651766ethyl 4-[(2S)-2-amino-5-tert-butoxy-5-oxopentanoyl]piperazine-1-carboxylateHCID 68599020Quinoline-2,4-dicarboxylic acid 4-ethyl ester

Product 1

HCID 685997922-[(S)-3-tert-Butoxycarbonyl-1-(4-ethoxycarbonyl-piperazine-1-carbonyl)-propylcarbamoyl]-quinoline-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g of Quinoline-2,4-dicarboxylic acid 4-ethyl ester and 2.8 g of 4-((S)-2-Amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 21 ml of DMF, 1.3 g of HOBT and 1.6 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 DCM. 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: 1.1 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 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-a594b7b81ebe487ca252d17ce34a5c7f
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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