1,2-Dichloroethane → HCID 178473385, compound

HRID 1185435Notes

Reaction equation

HRID 1185435 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.[CH2:15]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:38])[C@@H:27]([NH2:37])[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:22][CH2:21]1)=[O:19])[CH3:16].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:15]([O:17][C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:26](=[O:38])[C@@H:27]([NH:37][C:12]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[O:14])[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:24][CH2:25]1)=[O:19])[CH3:16]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 66651766ethyl 4-[(2S)-2-amino-5-tert-butoxy-5-oxopentanoyl]piperazine-1-carboxylateHCID 178418933HCID 178418933, compound

Product 1

HCID 178473385HCID 178473385, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.7 g 4-Hydroxy-quinoline-2-carboxylic acid and 5 g of 4-((S)-2-Amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 25 ml of DMF, 2.2 g of HOBT and 2.8 g of EDC was added and the reaction mixture was stirred for 3 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 n-heptane/ethyl acetate and dried under reduced pressure. Yield: 7.2 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 n-heptane/ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6904490422e643b38c49c61f0f98098d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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