1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86598954, compound

HRID 2220422Notes

Reaction equation

HRID 2220422 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:34][C@H:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[C:20]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:43]([S:46]([NH2:49])(=[O:48])=[O:47])[CH2:44][CH3:45].N12CCCN=C1CCCCC2>CN(C)C=O.C(OCC)(=O)C>[CH:28]1([O:27][C:20]2[CH:19]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][N:8]([CH2:34][C@H:35]([OH:42])[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:13][CH:14]=3)[CH:23]=[CH:22][C:21]=2[C:24]([NH:49][S:46]([CH2:43][CH2:44][CH3:45])(=[O:48])=[O:47])=[O:26])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3401849Propane-1-sulphonamideHCID 69102892HCID 69102892, compound

Product 1

HCID 86598954HCID 86598954, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]propyl]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid (133 mg) in N,N-dimethylformamide (1.3 ml) was added N,N′-carbonyldiimidazole (41.3 mg) and the mixture was stirred at room temperature for 5 hours. To the mixture were added 1-propanesulfonamide (31.4 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (41.6 μl) and the mixture was stirred at 50° C. for 14 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml×2) and brine (10 ml). The solution was dried over magnesium sulfate then concentrated in vacuo to give a crude solid which was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give tert-butyl [3-[3′-(cyclohexyloxy)-4′-[[(propylsulfonyl)amino]carbonyl]-4-biphenylyl]propyl][(2R)-2-hydroxy-2-phenylethyl]carbamate (63.5 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at 50° C. for 14 hours
  2. temperatureAfter cooling to room temperature
  3. washwashed with water (10 ml×2) and brine (10 ml)
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationthen concentrated in vacuo
  6. customto give a crude solid which
  7. customwas chromatographed on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3c276a7e196e4d749cd6792e92497a9c
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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