Hydrochloric Acid → HCID 67098022, compound

HRID 2078655Notes

Reaction equation

HRID 2078655 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:30][C@@H:31]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[C:19]([S:26][CH:27]([CH3:29])[CH3:28])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([S:51]([NH2:54])(=[O:53])=[O:52])[CH:46]=1.C1CCN2C(=NCCC2)CC1.Cl>CN(C)C=O.C(OCC)(=O)C>[CH:27]([S:26][C:19]1[CH:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][N:8]([CH2:30][C@@H:31]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:16][CH:15]=2)[CH:22]=[CH:21][C:20]=1[C:23]([NH:54][S:51]([C:47]1[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=1)(=[O:53])=[O:52])=[O:24])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 232710pyridine-3-sulfonamideHCID 67097735HCID 67097735, compound

Product 1

HCID 67098022HCID 67098022, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-3-(isopropylthio)-4-biphenylcarboxylic acid (500 mg) in N,N-dimethylformamide (5 ml) was added N,N′-carbonyldiimidazole (157 mg) and stirred at room temperature for 30 minutes. To the mixture were added 3-pyridinesulfonamide (153 mg) and 1,8-diazabicyclo[5.4.0]-7-undecene (145 μl) and stirred at room temperature for 3 hours. The reaction mixture was poured into 0.1N hydrochloric acid and ethyl acetate and the organic layer was separated. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel column chromatography to give tert-butyl [2-[3′-(isopropylthio)-4′-[[(3-pyridylsulfonyl)amino]carbonyl]-4-biphenylyl]-ethyl][(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]carbamate (613 mg).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-af7a096af7644c1fab2d86dca1641371
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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