4-(p-Fluorophenyl)butyric acid → HCID 68857413, compound

HRID 1782747Notes

Reaction equation

HRID 1782747 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.[Br:14][C:15]1[CH:16]=[C:17]([CH:54]=[C:55]([Br:58])[C:56]=1[OH:57])[CH2:18][C@H:19]([C:21]([NH:23][C@H:24]([C:40]([N:42]1[CH2:47][CH2:46][N:45]([C:48]2[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=2)[CH2:44][CH2:43]1)=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32]CC1C=CC=CC=1)=[O:31])=[O:22])[NH2:20].CN(C(ON1N=NC2C=C[CH:72]=[CH:73][C:68]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:81]CN(C(C)C)C(C)C>CN(C)C=O.O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:20][C@@H:19]([C:21]([NH:23][C@H:24]([C:40]([N:42]2[CH2:47][CH2:46][N:45]([C:48]3[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=3)[CH2:44][CH2:43]2)=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:73]([CH3:72])([CH3:68])[CH3:81])=[O:31])=[O:22])[CH2:18][C:17]2[CH:54]=[C:55]([Br:58])[C:56]([OH:57])=[C:15]([Br:14])[CH:16]=2)=[O:13])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 685244-(p-Fluorophenyl)butyric acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11527827HCID 11527827, compound

Product 1

HCID 68857413HCID 68857413, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.18 g (0.001 mol) 4-(4-fluorophenyl)-butanoic acid in a mixture of 4 ml of dimethylformamide and 10 ml of tetrahydrofuran was added with stirring a mixture of 0.71 g (0.001 mol) 1-[N2-(3,5-dibromo-D-tyrosyl)-N6-[(phenylmethoxy)carbonyl]-L-lysyl]-4-(4-pyridinyl)-piperazine, 0.32 g (0.001 mol) TBTU and 0.13 g (0.001 mol) DIEA and the mixture was stirred in a nitrogen atmosphere for 2 days. The reaction mixture was then evaporated down in vacuo and the remaining residue was taken up in dichloromethane. The organic phase was with 20% aqueous citric acid solution and then extracted with 10% aqueous sodium hydrogen carbonate solution, dried over sodium sulphate, filtered and evaporated down in vacuo. After stirring the residue with ether 0.68 g (77% of theory) of the desired product remain as an amorphous residue.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred in a nitrogen atmosphere for 2 days
  3. customThe reaction mixture was then evaporated down in vacuo
  4. extractionextracted with 10% aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated down in vacuo
  8. stirringAfter stirring the residue with ether 0.68 g (77% of theory) of the desired product

Sources & evidence

ORD record
ord-a6342fa8a1b5464a94e013d7dbe0e933
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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