Triethylamine → HCID 131736531, compound

HRID 1478790Notes

Reaction equation

HRID 1478790 reaction equation
[N:1](CCCCCNCCCCCN=[N+]=[N-])=[N+:2]=[N-:3].[OH:18][C:19]([CH2:21][CH2:22][CH2:23][CH2:24][C@H:25]1[C@@H:33]2[C@@H:28]([NH:29][C:30]([NH:32]2)=[O:31])[CH2:27][S:26]1)=[O:20].C1CN([P+](O[N:51]2[N:59]=[N:58]C3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[N-:1]=[N+:2]=[N-:3].[N-:58]=[N+:59]=[N-:51].[OH:20][C:19]([CH2:21][CH2:22][CH2:23][CH2:24][C@H:25]1[C@@H:33]2[C@@H:28]([NH:29][C:30]([NH:32]2)=[O:31])[CH2:27][S:26]1)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 171548BiotinHCID 2724699PyBOPHCID 123950995HCID 123950995, compound

Product 1

HCID 131736531HCID 131736531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of di(5-azidopentyl)amine (0.12 g, 0.49 mmol) in anhydrous DMF (5 mL) of were added biotin (0.12 g, 0.41 mmol), PyBOP (0.25 g, 0.49 mmol) and Et3N (0.23 mL, 1.64 mmol). The mixture was stirred for 22 h at room temperature under argon, and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, CH2Cl2/MeOH=13:1) to give biotin-diazide compound 25 (0.15 g, 79%). C20H35N9O2S; pale yellow oil; 1H NMR (CDCl3, 600 MHz) δ 4.48 (dd, J=7, 5 Hz, 1 H), 4.29 (dd, J=7, 5 Hz, 1 H), 3.28 (t, J=7 Hz, 4 H), 3.25 (t, J=7 Hz, 4 H), 3.20 (t, J=7 Hz, 2 H), 2.89 (dd, J=12, 5 Hz, 1 H), 2.71 (d, J=12 Hz, 1 H), 2.29 (t, J=7 Hz, 2H), 1.84 (br s, 3 H), 1.50-1.67 (m, 8 H), 1.43-1.44 (m, 2 H), 1.32-1.38 (m, 4 H); 13C NMR (CDCl3, 150 MHz) δ 172.4, 163.2, 61.8, 60.1, 55.3, 51.2, 47.0, 46.2, 45.6, 40.5, 32.5, 28.7, 28.6, 28.3, 27.3, 26.4, 25.1, 24.1. ESI-HRMS calcd for C20H36N9O2S: 466.2707, found: m/z 466.2703 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel, CH2Cl2/MeOH=13:1)

Sources & evidence

ORD record
ord-fbdfa62840884375b0ebb5444466e85e
Source dataset
uspto-grants-2016_08
Patent number
US09403855B2

Reaction notes

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