Triethylamine → HCID 86612515, compound

HRID 1432340Notes

Reaction equation

HRID 1432340 reaction equation
C(O[C:6](=[O:25])[NH:7][C@@H:8]([CH2:21][CH:22]([CH3:24])[CH3:23])[C@@H:9]([OH:20])[CH2:10][C@H:11]([C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:12])(C)(C)C.[Cl:26][C:27]1[CH:44]=[CH:43][C:30]2[C:31](C(O)=O)=[CH:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[O:35][C:29]=2[CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>Cl.O1CCOCC1.C(Cl)Cl>[CH2:15]([NH:14][C:13]([C@H:11]([CH3:12])[CH2:10][C@H:9]([OH:20])[C@@H:8]([NH:7][C:6]([C:31]1[C:30]2[CH:43]=[CH:44][C:27]([Cl:26])=[CH:28][C:29]=2[O:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[CH:32]=1)=[O:25])[CH2:21][CH:22]([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18663611HCID 18663611, compoundHCID 86612516HCID 86612516, compound

Product 1

HCID 86612515HCID 86612515, compoundYield 54.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

((1S,2S,4R)-4-Butylcarbamoyl-2-hydroxy-1-isobutyl-pentyl)-carbamic acid tert-butyl ester (66 mg, 0.18 mmol) are dissolved in 4N HCl in dioxane (3 ml). After stirring for 1 h at rt the solvent is evaporated and the residue dried in vacuum. The residue is dissolved in DCM (3 ml) and 7-Chloro-dibenzo[b,f]oxepine-10-carboxylic acid (60 mg, 0.22 mmol, 1.2 eq), HOBT (30 mg, 0.22 mmol, 1.2 eq), EDCl (53 mg, 0.28 mmol, 1.5 eq) and triethylamine (0.077 ml, 0.55 mmol, 3 eq) are added. The mixture is stirred over night at rt. The reaction mixture is diluted with DCM and washed with water, bicarbonate and brine. The organic layer is dried over magnesium sulfate and the solvent is evaporated. Purification on silica (Flashmaster, DCM/methanol 100%→90%) and crystallization from DCM/hexane gives the products as white crystals (50 mg).

Workup

  1. customis evaporated
  2. customthe residue dried in vacuum
  3. dissolutionThe residue is dissolved in DCM (3 ml)
  4. stirringThe mixture is stirred over night at rt
  5. washwashed with water, bicarbonate and brine
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. customthe solvent is evaporated
  8. customPurification
  9. customon silica (Flashmaster, DCM/methanol 100%→90%) and crystallization from DCM/hexane

Sources & evidence

ORD record
ord-e4d786327b4f401aac63a50ae2f61fe6
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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