1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178457761, compound

HRID 2212250Notes

Reaction equation

HRID 2212250 reaction equation
CO[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N:4][S:5]([CH3:8])(=[O:7])=[O:6].[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH:24]([OH:40])[CH:25]([NH:28][C:29](=[O:39])[CH:30]([NH2:38])[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH2:26][CH3:27].C1CCN2C(=NCCC2)CC1>C(#N)C>[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH:24]([OH:40])[CH:25]([NH:28][C:29](=[O:39])[CH:30]([NH:38][C:3](=[N:4][S:5]([CH3:8])(=[O:6])=[O:7])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21962749HCID 21962749, compoundHCID 69616474HCID 69616474, compound

Product 1

HCID 178457761HCID 178457761, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-(methoxy-phenyl-methylene)methansulfonamide (250 mg, 0.616 mmol) and 2-amino-3-cyclohexylpropionic acid [1-(benzoxazol-2-ylhydroxymethyl)-propyl]amide (255 mg, 0.616 mmol) in dry acetonitile (4 mL) at room temperature was added DBU (0.37 mL, 2.46 mmol), and the mixture was stirred at the same temperature overnight. After a removal of the solvent, the reaction mixture was partitioned between ethyl acetate and 1N-HCl solution, washed brine and then water. The organic extracts were dried, concentrated in vacuo, and purified by flash chromatography on silica gel (eluted with EtOAc/hexanes=3/1) to yield 250 mg of N-[1-(benzoxazol-2-yl-hydroxymethyl)propyl]-3-cyclohexyl-2-[(methanesulfonyliminophenylmethyl)amino]-propionamide.

Workup

  1. customAfter a removal of the solvent
  2. customthe reaction mixture was partitioned between ethyl acetate and 1N-HCl solution
  3. washwashed brine
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on silica gel (eluted with EtOAc/hexanes=3/1)

Sources & evidence

ORD record
ord-add08cc45b8647e08eb19c9c62a249bb
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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