Diisopropylethylamine → HCID 117625176, compound

HRID 515652Notes

Reaction equation

HRID 515652 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].O[N:18]=[C:19]([NH2:35])[CH2:20][CH2:21][CH2:22][CH2:23][N:24]1[C:28]2[CH:29]=[C:30]([CH3:33])[CH:31]=[CH:32][C:27]=2[O:26][C:25]1=[O:34].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.ClCCl>[O:14]=[C:13]1[NH:12][C@H:11]2[CH2:10][S:9][C@@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:2]([O:1]/[N:18]=[C:19](\[NH2:35])/[CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:28]4[CH:29]=[C:30]([CH3:33])[CH:31]=[CH:32][C:27]=4[O:26][C:25]3=[O:34])=[O:3])[C@H:16]2[NH:15]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 171548BiotinHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 123617581HCID 123617581, compound

Product 1

HCID 117625176HCID 117625176, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of biotin 7 (23 mg, 0.092 mmol) and compound 13 (22 mg, 0.083 mmol) in anhydrous DMF (0.5 ml) was added EDCl (16 mg, 0.10 mmol) and DIPEA (13 mg, 0.10 mmol) and stirred under a nitrogen atmosphere at ambient temperature for 12 h. The reaction mixture was diluted with dichloromethane (25 ml) and washed with water (25 ml) and brine (25 ml). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 19:1 dichloromethane/methanol to give a yellow oil (21 mg, 51%).

Workup

  1. washwashed with water (25 ml) and brine (25 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 19:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-e8715723a0e1404694bb3a133e42c727
Source dataset
uspto-grants-2015_08
Patent number
US09108978B2

Reaction notes

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