1,2-Dichloroethane → HCID 178473381, compound

HRID 1908623Notes

Reaction equation

HRID 1908623 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:40])[C@@H:28]([NH2:39])[CH2:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:23][CH2:22]1)=[O:20])[CH3:17].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:16]([O:18][C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:40])[C@@H:28]([NH:39][C:13]([C:4]2[CH:3]=[C:2]([OH:1])[N:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:5]=2)=[O:15])[CH2:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:25][CH2:26]1)=[O:20])[CH3:17]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 669199764-((S)-2-Amino-5-tert-butoxycarbonyl-pentanoyl)-piperazine-1-carboxylic acid ethyl esterHCID 178524628HCID 178524628, compound

Product 1

HCID 178473381HCID 178473381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 171 mg of 5-Hydroxy-1-phenyl-1H-pyrazole-3-carboxylic acid and 300 mg of 4-((S)-2-Amino-5-tert-butoxycarbonyl-pentanoyl)-piperazine-1-carboxylic acid ethyl ester in 3 ml of DMF, 128 mg of HOBT and 160 mg of EDC was added and the reaction mixture was stirred for 5 h at RT. Then, the reaction mixture was diluted with water and filtered through a Chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure. The solid product was triturated with DCM and the precipitate was dried under reduced pressure. The crude product was used in the subsequent reaction.

Workup

  1. filtrationfiltered through a Chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customThe solid product was triturated with DCM
  5. customthe precipitate was dried under reduced pressure
  6. customThe crude product was used in the subsequent reaction

Sources & evidence

ORD record
ord-2054c1a39ada407d981ca260ecbdea4d
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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