Triethylamine → HCID 131723965, compound

HRID 1356984Notes

Reaction equation

HRID 1356984 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH:11]([OH:24])[CH:10]([CH:25]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:41][C:42]1[CH:50]=[CH:49][C:45]([C:46](Cl)=[O:47])=[CH:44][CH:43]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH:11]([OH:24])[CH:10]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4].[Cl:41][C:42]1[CH:50]=[CH:49][C:45]([C:46]([O-:5])=[O:47])=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 18504713HCID 18504713, compound

Product 1

HCID 131723965HCID 131723965, compoundYield 140.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 3,7-di(tert-butoxycarbonyl)-3,7-diazabicyclononan-9-ol (475 mg, 1.39 mmol) in methylene chloride (25 mL) was added triethylamine (0.390 mL), 4-chlorobenzoyl chloride (0.23 mL, 1.81 mmol), and 4-dimethylaminopyridine (221 mg, 1.81 mmol). The reaction mixture was stirred for 2.5 h and was then diluted with methylene chloride and washed with 0.5N aqueous HCl and water. After drying over sodium sulfate the solution was concentrated and the residue was purified by column chromatography on silica gel with 25% ethyl acetate in hexanes to give the title compound (611 mg, 91%). 1H NMR (300 MHz, CDCl3) 1.18 (s, 18H), 1.80 (s, 3H), 3.00 (t, 2H), 3.31 (t, 2H), 3.99 (m, 3H), 4.30 (m, 2H); mass spectrum m/z 365 (M+Na)+.

Workup

  1. washwashed with 0.5N aqueous HCl and water
  2. dry with materialAfter drying over sodium sulfate the solution
  3. concentrationwas concentrated
  4. customthe residue was purified by column chromatography on silica gel with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fbec27f4536e4da893a8b410fd51257c
Source dataset
uspto-grants-2003_07
Patent number
US06589934B1

Reaction notes

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