Diisopropylethylamine → HCID 46917268, compound

HRID 928912Notes

Reaction equation

HRID 928912 reaction equation
[N:1](CCOCCON)=[N+:2]=[N-:3].[OH:11][C:12]([CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]1[C@@H:26]2[C@@H:21]([NH:22][C:23]([NH:25]2)=[O:24])[CH2:20][S:19]1)=[O:13].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:1]([CH:14]([CH2:15][CH2:16][CH2:17][C@H:18]1[C@@H:26]2[C@@H:21]([NH:22][C:23]([NH:25]2)=[O:24])[CH2:20][S:19]1)[C:12](=[O:11])[OH:13])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 171548BiotinHCID 2724699PyBOPHCID 58989132Aminooxy-PEG1-azide

Product 1

HCID 46917268HCID 46917268, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of O-(2-(2-azidoethoxy)ethyl)hydroxylamine (10 mg, 0.068 mmol), biotin (225 mg, 0.103 mmol) and DIPEA (29 mg, 0.206 mmol) in 0.8 mL of DMF was added PyBOP (54 mg, 0.103 mmol). The reaction was allowed to stir at room temperature for 2 h. Solvent was then removed in vacuo, and the crude product was purified by silica gel column chromatography (ethyl acetate: methanol 4:1) to afford azido-biotin (22 mg, 0.059 mmol, 88%) as a pale yellow solid. 1H NMR (CD3OD, 500 MHz) δ (ppm): 1.35 (m, 1H), 1.43 (m, 2H), 1.68 (stack, 4H), 2.11 (t, J=7.3 Hz, 2H), 2.70 (d, J=12.8 Hz, 1H), 2.92 (dd, J=5.0, 12.8 Hz, 1H), 3.20 (m, 1H), 3.43 (m, 2H), 3.67 (m, 2H), 3.72 (m, 2H), 3.98 (m, 2H), 4.30 (m, 1H), 4.48 (m, 1H).

Workup

  1. customSolvent was then removed in vacuo
  2. customthe crude product was purified by silica gel column chromatography (ethyl acetate: methanol 4:1)

Sources & evidence

ORD record
ord-37bc56eea48e4640a7424fd60a0713bc
Source dataset
uspto-grants-2016_03
Patent number
US09290791B2

Reaction notes

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