Triethylamine → Dibenzo[b,f]oxepine-10-carboxylic acid [(1S*,2S*,4R*)-1-(3-benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-amide

HRID 1432337Notes

Reaction equation

HRID 1432337 reaction equation
[Cl-].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][CH:30]=1)[CH2:13][C@H:14]([NH3+:27])[C@@H:15]([OH:26])[CH2:16][C@H:17]([C:19](=[O:25])[NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:31]1[C:41]2[CH:40]=[C:39]([C:42](O)=[O:43])[C:38]3[CH:45]=[CH:46][CH:47]=[CH:48][C:37]=3[O:36][C:35]=2[CH:34]=[CH:33][CH:32]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][CH:30]=1)[CH2:13][C@H:14]([NH:27][C:42]([C:39]1[C:38]2[CH:45]=[CH:46][CH:47]=[CH:48][C:37]=2[O:36][C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:41]=2[CH:40]=1)=[O:43])[C@@H:15]([OH:26])[CH2:16][C@H:17]([C:19](=[O:25])[NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:18])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 859640Dibenzo[b,f]oxepine-10-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86612512(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl-ammonium chloride

Product 1

HCID 86612513Dibenzo[b,f]oxepine-10-carboxylic acid [(1S*,2S*,4R*)-1-(3-benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-amideYield 80.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl-ammonium chloride (210 mg, 0.48 mmol), Dibenzo[b,f]oxepine-10-carboxylic acid (138 mg, 0.58 mmol, 1.2 eq), EDCl (139 mg, 0.72 mmol, 1.5 eq), HOBt (78 mg, 0.58 mmol, 1.2 eq) and triethylamine (0.20 ml, 1.4 mmol, 3 eq) are dissolved in DCM (12 ml) and stirred at rt for 3 days. EtOAc is added. After washing with 0.5 N HCl, brine, bicarbonate and brine again, drying over magnesium sulfate, the solvent is evaporated and the residue recrystallized from DCM/ether/hexane with a drop of methanol to give a white solid (240 mg).

Workup

  1. washAfter washing with 0.5 N HCl, brine, bicarbonate and brine again
  2. dry with materialdrying over magnesium sulfate
  3. customthe solvent is evaporated
  4. customthe residue recrystallized from DCM/ether/hexane with a drop of methanol

Sources & evidence

ORD record
ord-7acc5f9a12a4442999f0e9fd14729769
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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