Triethylamine → HCID 78323439, compound

HRID 2276286Notes

Reaction equation

HRID 2276286 reaction equation
O[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.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CCN(CC)CC.[F:47][C:48]1[CH:62]=[CH:61][CH:60]=[C:59]([F:63])[C:49]=1/[CH:50]=[CH:51]/[C:52]1[CH:58]=[CH:57][C:55]([NH2:56])=[CH:54][CH:53]=1>CN(C=O)C.O>[F:47][C:48]1[CH:62]=[CH:61][CH:60]=[C:59]([F:63])[C:49]=1/[CH:50]=[CH:51]/[C:52]1[CH:53]=[CH:54][C:55]([NH:56][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]2[CH:16]3[CH:11]([NH:12][C:13](=[O:14])[NH:15]3)[CH2:10][S:9]2)=[CH:57][CH:58]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 171548BiotinHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68153934HCID 68153934, compound

Product 1

HCID 78323439HCID 78323439, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 100 mg (0.41 mmol 1 equiv) of biotin in 3 mL of anhydrous DMF was added 66 mg (0.49 mmol, 1.2 equiv) of 1-hydroxybenzotriazole hydrate, 94 mg (0.49 mmol, 1.2 equiv) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, and 79 mg (0.78 mmol, 1.9 equiv) of Et3N. The mixture was stirred for 10 min, and 95 mg (0.41 mmol) of 9 was added. The mixture was stirred for 24 h at 25° C. and poured into water. The precipitate was collected by filtration and chromatographed using 1:1 EtOAc-MeOH to give 120 mg (66%) of 11 as white crystals: mp 278-280° C. 1H NMR (DMSO-d6): δ 9.99 (s, 1H), 7.64 (d, 2H, J=8.8 Hz), 7.56 (d, 2H, J=8.8 Hz), 7.37-7.29 (m, 2H), 7.19-7.12 (m, 2H), 7.02 (d, 1H, J=16.4 Hz), 6.44 (s, 1H), 6.36 (s, 1H), 4.33-4.29 (m, 1H), 4.16-4.13 (m, 1H), 3.15-3.10 (m, 1H), 2.83 (dd, 1H, J1=12.8 Hz, J2=4.8 Hz), 2.58 (d, 1H, J=12.0 Hz), 2.33 (t, 2H, J=7.2 Hz), 1.70-1.33 (m, 6H). 13C NMR (DMSO-d6): δ 171.70, 163.13, 160.53 (dd, J1=247.8 Hz, J2=7.7 Hz, two C), 140.09, 135.28 (t, J=7.9 Hz), 131.77, 129.18 (t, J=10.7 Hz), 127.69 (two C), 119.54 (two C), 114.61 (t, J=15.5 Hz), 113.25, 112.45 (dd, J1=19.1 Hz, J2=6.3 Hz, two C), 61.48, 59.63, 55.82, 40.28, 36.70, 28.67, 28.53, 25.50. HRMS (EI) Calcd for C24H25F2N3O2S: 457.1636. Found: 457.1650. Anal. Calcd for C24H25F2N3O2S: C, 63.00; H, 5.51. Found: C, 62.82; H, 5.47.

Workup

  1. stirringThe mixture was stirred for 24 h at 25° C.
  2. filtrationThe precipitate was collected by filtration
  3. customchromatographed

Sources & evidence

ORD record
ord-f3195088df564284974c163cfc3bac6e
Source dataset
uspto-grants-2015_09
Patent number
US09132102B2

Reaction notes

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