1,2-Dichloroethane → HCID 68601559, compound

HRID 1185447Notes

Reaction equation

HRID 1185447 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:41])[C@@H:13]([NH:22][C:23]([C:25]2[CH:34]=[C:33]([O:35][CH2:36][C:37]([OH:39])=O)[C:32]3[C:27](=[CH:28][C:29]([CH3:40])=[CH:30][CH:31]=3)[N:26]=2)=[O:24])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(Cl)CCl.FC1C(O)=C(F)C(F)=C(F)C=1F.FC(F)(F)C(O)=O.[CH2:65]([NH:67][C:68]([C@@H:70]1[CH2:74][CH2:73][CH2:72][NH:71]1)=[O:69])[CH3:66]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:41])[C@@H:13]([NH:22][C:23]([C:25]2[CH:34]=[C:33]([O:35][CH2:36][C:37]([N:71]3[CH2:72][CH2:73][CH2:74][C@H:70]3[C:68](=[O:69])[NH:67][CH2:65][CH3:66])=[O:39])[C:32]3[C:27](=[CH:28][C:29]([CH3:40])=[CH:30][CH:31]=3)[N:26]=2)=[O:24])[CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 68599627HCID 68599627, compoundHCID 68600133HCID 68600133, compound

Product 1

HCID 68601559HCID 68601559, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 80 mg of 4-{(S)-3-tert-Butoxycarbonyl-2-[(4-carboxymethoxy-7-methyl-quinoline-2-carbonyl)-amino]-propionyl}-piperazine-1-carboxylic acid ethyl ester in 8 ml of DMF, 33 mg of EDC, 32 mg of pentafluorophenol and 24 mg of NEM was added and the reaction mixture was stirred for 2 h. Then, 39 mg of (S)-Pyrrolidine-2-carboxylic acid ethylamide trifluoroacetate and 20 mg of NEM in 5 ml of DMF was added. After 1 h the reaction mixture was diluted with water. After filtration through a chem Elut® cartridge by eluting with ethyl acetate the solvents were removed under reduced pressure. The isolated crude product was pure enough for the next reaction step.

Workup

  1. filtrationAfter filtration through a chem Elut® cartridge
  2. washby eluting with ethyl acetate the solvents
  3. customwere removed under reduced pressure
  4. customThe isolated crude product
  5. customwas pure enough for the next reaction step

Sources & evidence

ORD record
ord-950328af70c54466bc6c5f74f3fff6a5
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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