Hydrochloric Acid → HCID 86598960, compound

HRID 2220433Notes

Reaction equation

HRID 2220433 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][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24](O)=[O:25])=[C:19]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:55][S:56]([NH2:59])(=[O:58])=[O:57].C1CCN2C(=NCCC2)CC1.Cl>CN(C)C=O>[CH:28]1([O:27][C:19]2[CH:18]=[C:17]([C:14]3[CH:15]=[CH:16][C: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]([CH3:4])([CH3:3])[CH3:2])=[CH:12][CH:13]=3)[CH:22]=[CH:21][C:20]=2[CH2:23][C:24]([NH:59][S:56]([CH3:55])(=[O:58])=[O:57])=[O:25])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69103161HCID 69103161, compound

Product 1

HCID 86598960HCID 86598960, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(cyclohexyloxy)-4-biphenylyl]acetic acid (228 mg) in N,N-dimethylformamide (2.5 ml) was added 1,1′-carbonyldiimidazole (77 mg) at room temperature under nitrogen, and the mixture was stirred at the same temperature for 1.5 hours. To this one were added methanesulfonamide (76 mg) and 1,8-diazabicyclo[5.4.0]-7-undecene (91 mg) at 5° C., and the mixture was stirred at the same temperature for 5 hours. The resulting mixture was poured into 1N hydrochloric acid and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid (twice) and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=10:1 to 5:1) to give tert-butyl [2-(3′-(cyclohexyloxy)-4′-[2-[(methylsulfonyl)amino]-2-oxoethyl]-4-biphenylyl]ethyl]-[(2R)-2-hydroxy-2-phenylethyl]carbamate (61 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed successively with 1N hydrochloric acid (twice) and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-332065ea00654d3d88e6ef41485f0702
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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