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1,2-Dichloroethane → HCID 178452371, compound

HRID 1185469
Notes
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Reaction equation

HRID 1185469 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.FC(F)(F)C(O)=O.[CH2:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35](=[O:48])[C@@H:36]([NH2:47])[CH2:37][CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:31][CH2:30]1)=[O:28])[CH2:23][CH2:24][CH3:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:22]([O:26][C:27]([N:29]1[CH2:30][CH2:31][N:32]([C:35](=[O:48])[C@@H:36]([NH:47][C:12]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[O:14])[CH2:37][CH2:38][O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:33][CH2:34]1)=[O:28])[CH2:23][CH2:24][CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 685991994-((S)-2-Amino-4-benzyloxy-butyryl)-piperazine-1-carboxylic acid butyl ester trifluoroacetateHCID 178418933HCID 178418933, compound

Product 1

HCID 178452371HCID 178452371, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g of 4-Hydroxy-quinoline-2-carboxylic acid and 2.6 g of 4-((S)-2-Amino-4-benzyloxy-butyryl)-piperazine-1-carboxylic acid butyl ester trifluoroacetate in 12 ml of DMF, 0.8 g of HOBT, 1.0 g of EDC and 1.2 g of NEM was added and the reaction mixture was stirred for 16 h at RT. Then, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was precipitated from a mixture of n-heptane and ethyl acetate. The precipitated product was collected by filtration and dried under reduced pressure. The isolated product was pure enough for the next reaction step. Yield: 900 mg.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was precipitated from a mixture of n-heptane and ethyl acetate
  5. filtrationThe precipitated product was collected by filtration
  6. customdried under reduced pressure
  7. customThe isolated product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-557eb106da214803a98ec91c0222d83c
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669266B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes