Diethylamine → HCID 54309628, compound

HRID 1782749Notes

Reaction equation

HRID 1782749 reaction equation
[NH2:1][C:2]1[C:30]([Br:31])=[CH:29][C:5]([CH2:6][C@H:7]([C:26]([OH:28])=O)[NH:8]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:4][C:3]=1[Br:32].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:74][C:75]([CH3:92])([O:77][C:78]([N:80]1[CH2:85][CH2:84][CH:83]([CH:86]2[CH2:91][CH2:90][NH:89][CH2:88][CH2:87]2)[CH2:82][CH2:81]1)=[O:79])[CH3:76].C(NCC)C>O1CCCC1>[NH2:1][C:2]1[C:3]([Br:32])=[CH:4][C:5]([CH2:6][C@H:7]([C:26]([N:89]2[CH2:88][CH2:87][CH:86]([CH:83]3[CH2:82][CH2:81][N:80]([C:78]([O:77][C:75]([CH3:92])([CH3:76])[CH3:74])=[O:79])[CH2:85][CH2:84]3)[CH2:91][CH2:90]2)=[O:28])[NH2:8])=[CH:29][C:30]=1[Br:31]

Participants

8

Reactant 6

HCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 117475994,4'-Bipiperidine, 1-boc protectedHCID 68933224HCID 68933224, compound

Product 1

HCID 54309628HCID 54309628, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.60 g (0.01 mol) of 4-amino-3,5-dibromo-N -(9-fluorenylmethoxycarbonyl)-D-phenylalanine, 1.35 g (0.01 mol) HOBt, 3.21 g (0.01 mol) TBTU, 1.29 g (0.01 mol) DIEA, 2.68 g (0.01 mol) 4-[1-(1,1-dimethylethoxycarbonyl)-4-piperidinyl]-piperidine and 150 ml of tetrahydrofuran was stirred for 2 hours at room temperature. After the reaction was complete 20 ml of diethylamine were added and the mixture was stirred for a further 18 hours at room temperature. The reaction mixture was evaporated down in vacuo, the residue was taken up in 200 ml of dichloromethane and washed successively with 100 ml of saturated sodium chloride solution and saturated sodium hydrogen carbonate solution and dried over magnesium sulphate. The reddish oil remaining after elimination of the solvent was purified by column chromatography on silica gel (30-60 μm) using firstly dichloromethane, then FM4 as eluant. The title compound was obtained in the form of a colourless amorphous substance and in a yield of 4.31 g (73.3% of theory).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for a further 18 hours at room temperature
  3. customThe reaction mixture was evaporated down in vacuo
  4. washwashed successively with 100 ml of saturated sodium chloride solution and saturated sodium hydrogen carbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customwas purified by column chromatography on silica gel (30-60 μm)

Sources & evidence

ORD record
ord-55f41c892ab54a1eb0c91988fb9eb7a7
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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