Diisopropylethylamine → HCID 54391593, compound

HRID 1264310Notes

Reaction equation

HRID 1264310 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.[CH3:55][O:56][C:57](=[O:72])[C:58]1[CH:63]=[CH:62][C:61]([C:64]2[CH:69]=[CH:68][N:67]=[C:66]([CH2:70][NH2:71])[CH:65]=2)=[CH:60][CH:59]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:71][CH2:70][C:66]2[CH:65]=[C:64]([C:61]3[CH:62]=[CH:63][C:58]([C:57]([O:56][CH3:55])=[O:72])=[CH:59][CH:60]=3)[CH:69]=[CH:68][N:67]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70025544HCID 70025544, compound

Product 1

HCID 54391593HCID 54391593, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (275 mg, 1.2 mmol) in CH2Cl2 (2 ml) was added diisopropylethylamine (0.23 ml, 1.32 mmol). The resulting solution was stirred for 5 minutes then TBTU (337 mg, 1.26 mmol) was added and stirred for 20 minutes. To the reaction mixture was added a solution of 4-(2-aminomethyl-pyridin-4-yl)-benzoic acid methyl ester trifluoroacetic acid salt (356 mg, 1 mmol, reference example 103a) and diisopropylethylamine (0.192 ml, 1.1 mmol) in CH2Cl2 (2 ml). The reaction mixture was stirred 45 minutes then concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 40% ethyl acetate/10% methanol/hexanes) to give 455 mg of product as a white foam. MS (ion spray) m/z 454 (M+H)+.

Workup

  1. stirringstirred for 20 minutes
  2. stirringThe reaction mixture was stirred 45 minutes
  3. concentrationthen concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (eluting with 40% ethyl acetate/10% methanol/hexanes)

Sources & evidence

ORD record
ord-a5656899ee1f4f5997fcc1a30d5ceca9
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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