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1,2-Dichloroethane → HCID 178473389, compound

HRID 1970436
Notes
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Reaction equation

HRID 1970436 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:40])[C@@H:29]([NH2:39])[CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:24][CH2:23]1)=[O:21])[CH3:18].C(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:40])[C@@H:29]([NH:39][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])[CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:26][CH2:27]1)=[O:21])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 66651766ethyl 4-[(2S)-2-amino-5-tert-butoxy-5-oxopentanoyl]piperazine-1-carboxylateHCID 178524629HCID 178524629, compound

Product 1

HCID 178473389HCID 178473389, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 81531
Diisopropylethylamine
Solvent

Procedure

To a solution of 2.500 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 3.864 g 4-((S)-2-amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 20 ml DMF 1.723 g HOBt, 1.9 ml DIPEA and 2.157 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-ce22a6510ea1409887049644006311a3
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426420B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes