1,2-Dichloroethane → HCID 68600025, compound

HRID 1185483Notes

Reaction equation

HRID 1185483 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([NH:14][C:15]([C:17]1[CH:26]=[C:25]([O:27][CH2:28][C:29](O)=[O:30])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:33](Cl)CCl.FC1C(O)=C(F)C(F)=C(F)C=1F.FC(F)(F)C(O)=O.[CH:56]1([NH:59][C:60]([C@@H:62]2[CH2:66][CH2:65][CH2:64][NH:63]2)=[O:61])[CH2:58][CH2:57]1>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([NH:14][C:15]([C:17]1[CH:26]=[C:25]([O:27][CH2:28][C:29]([N:63]2[CH2:64][CH2:65][CH2:66][C@H:62]2[C:60](=[O:61])[NH:59][CH:56]2[CH2:58][CH2:57][CH2:33]2)=[O:30])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 68600476HCID 68600476, compoundHCID 68601518HCID 68601518, compound

Product 1

HCID 68600025HCID 68600025, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4 g of (S)-2-[(4-Carboxymethoxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester in 30 ml of DCM, 3.4 g of EDC and 3.2 g of pentafluorophenol was added and the reaction mixture was stirred for 2 h at RT. Then, 5 g of (S)-Pyrrolidine-2-carboxylic acid cyclopropylamide trifluoroacetate salt and 2 g of NEM in 10 ml of DCM was added. After 3 h the reaction mixture was diluted with water and extracted with DCM (3×150 ml). The combined organic phases were 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: 1.8 g.

Workup

  1. extractionextracted with DCM (3×150 ml)
  2. dry with materialThe combined organic phases were 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-11fda61f659e4870a54a7085a138301d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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