1,2-Dichloroethane → HCID 178473393, compound

HRID 1185471Notes

Reaction equation

HRID 1185471 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:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34](=[O:47])[C@@H:35]([NH2:46])[CH2:36][CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:30][CH2:29]1)=[O:27])[CH3:24].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34](=[O:47])[C@@H:35]([NH:46][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])[CH2:36][CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:30][CH2:29]1)=[O:27])[CH3:24]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 66856328HCID 66856328, compoundHCID 178418698HCID 178418698, compound

Product 1

HCID 178473393HCID 178473393, 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 1.7 g of 4-((S)-2-Amino-4-benzyloxy-butyryl)-piperazine-1-carboxylic acid ethyl ester trifluoroacetate in 15 ml of DMF, 566 mg of NEM, 753 mg of HOBT and 943 mg 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 precipitated from a mixture of n-heptane and ethyl acetate. The precipitated product was collected by filtration and dried under reduced pressure. The isolated product was pure enough for the next reaction step. Yield: 1.8 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 precipitated from a mixture of n-heptane and ethyl acetate
  5. filtrationThe precipitated product was collected by filtration
  6. customdried under reduced pressure
  7. customThe isolated product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-e0cfc69f45cf4bf9a6c79baedc550eea
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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