1,2-Dichloroethane → HCID 178473399, compound

HRID 1970441Notes

Reaction equation

HRID 1970441 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([OH:13])=[CH:11][C:10]([C:14]([OH:16])=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:17]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:39])[C@@H:29]([NH2:38])[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:24][CH2:23]1)=[O:21])[CH3:18].[CH2:40](Cl)CCl>CN(C=O)C.CCN(C(C)C)C(C)C>[CH2:17]([O:19][C:20]([N:22]1[CH2:23][CH2:24][N:25]([C:28](=[O:39])[C@@H:29]([NH:38][C:14]([C:10]2[CH:11]=[C:12]([OH:13])[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[N:9]=2)=[O:16])[CH:30]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH3:40])[CH2:26][CH2:27]1)=[O:21])[CH3:18]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 668549254-((S)-2-amino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl esterHCID 178524629HCID 178524629, compound

Product 1

HCID 178473399HCID 178473399, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 3.199 g 1-(3-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid (prepared by standard procedure using 3-fluorophenylhydrazine hydrochloride and sodium diethyl-2-oxosuccinate followed by ester hydrolysis) and 4.743 g 4-((S)-2-amino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester in 26 ml DMF 2.205 g HOBt, 2.5 ml DIPEA and 2.760 g EDC were added and the reaction mixture was stirred for 16 h at RT. Then the reaction mixture was evaporated, diluted with ethyl acetate and subsequently extracted with aqueous LiCl (4% w/w) and aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction.

Workup

  1. customThen the reaction mixture was evaporated
  2. additiondiluted with ethyl acetate
  3. extractionsubsequently extracted with aqueous LiCl (4% w/w) and aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c90b4a9a883347f4bb22bbb0d088f6a7
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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