N-(3-methoxyphenyl)piperazine → HCID 66854463, compound

HRID 1185473Notes

Reaction equation

HRID 1185473 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH3:47][O:48][C:49]1[CH:50]=[C:51]([N:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)[CH:52]=[CH:53][CH:54]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:10]([N:58]1[CH2:57][CH2:56][N:55]([C:51]2[CH:52]=[CH:53][CH:54]=[C:49]([O:48][CH3:47])[CH:50]=2)[CH2:60][CH2:59]1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81430N-(3-methoxyphenyl)piperazineHCID 1074725-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 66854463HCID 66854463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 2.7 g of NEM and 1.9 g of TOTU in 10 ml of DMF, 1.1 g of 1-(3-Methoxy-phenyl)-piperazine was added at RT and stirred for 16 h. The reaction mixture was diluted with 150 ml of ethyl and subsequently extracted with aqueous LiCl (4% w/w), 0.1 M HCl and aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was pure enough for the further manipulations. Yield: 4 g.

Workup

  1. additionThe reaction mixture was diluted with 150 ml of ethyl
  2. extractionsubsequently extracted with aqueous LiCl (4% w/w), 0.1 M HCl and aqueous NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0c2bf4a0de32481283f9a9790e832508
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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