Triethylamine → HCID 58124006, compound

HRID 536676Notes

Reaction equation

HRID 536676 reaction equation
CCN(CC)CC.F[B-](F)(F)F.[N:13]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=[N:14]1.[C:30]([O:34][C:35]([N:37]1[CH2:44][CH2:43][C@:42]2([CH3:47])[C@H:45]([CH3:46])[C@H:38]1[CH2:39][C:40]1[CH:51]=[CH:50][C:49]([C:52](O)=[O:53])=[CH:48][C:41]=12)=[O:36])([CH3:33])([CH3:32])[CH3:31].O.NN>CN(C)C=O.O>[C:30]([O:34][C:35]([N:37]1[CH2:44][CH2:43][C@:42]2([CH3:47])[C@H:45]([CH3:46])[C@H:38]1[CH2:39][C:40]1[CH:51]=[CH:50][C:49]([C:52]([NH:13][NH2:14])=[O:53])=[CH:48][C:41]=12)=[O:36])([CH3:32])([CH3:31])[CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58123640HCID 58123640, compound

Product 1

HCID 58124006HCID 58124006, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NEt3 (1.7 mL) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (3.9 g) are added in turn to a solution of (2R,6R,11S)-6,11-dimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3,8-dicarboxylic acid 3-tertbutyl ester (4.2 g) in dimethylformamide (10 mL). The resulting solution is stirred at ambient temperature for 30 min, before hydrazine hydrate (3 mL) is added. The solution is stirred further at room temperature for 1 h and then water (30 mL) is added. The resulting mixture is extracted with ethyl acetate and the combined organic extracts are washed with 1 M aqueous NaOH solution, water, and brine. After drying (MgSO4), the solvent is evaporated and the residue is purified by chromatography on silica gel (cyclohexane/EtOAc 1:4->0:1) to give the title compound.

Workup

  1. additionis added
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe combined organic extracts are washed with 1 M aqueous NaOH solution, water, and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent is evaporated
  6. customthe residue is purified by chromatography on silica gel (cyclohexane/EtOAc 1:4->0:1)

Sources & evidence

ORD record
ord-778f9de835e34a08ade48812dccea836
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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