Hydrochloric Acid → HCID 67098076, compound

HRID 2078665Notes

Reaction equation

HRID 2078665 reaction equation
[Si:1]([O:8][C@H:9]([C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1)[CH2:10][N:11]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([NH:35][S:36]([CH2:39][C:40]#[N:41])(=[O:38])=[O:37])=[O:34])=[C:29]([O:42][CH:43]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)[CH:28]=2)=[CH:23][CH:22]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-:56].[K+].[K+].OO.Cl>CS(C)=O>[NH2:41][C:40](=[O:56])[CH2:39][S:36]([NH:35][C:33]([C:30]1[CH:31]=[CH:32][C:27]([C:24]2[CH:23]=[CH:22][C:21]([CH2:20][CH2:19][N:11]([CH2:10][C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[C:49]3[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=3)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[CH:26][CH:25]=2)=[CH:28][C:29]=1[O:42][CH:43]1[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]1)=[O:34])(=[O:38])=[O:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67097125HCID 67097125, compound

Product 1

HCID 67098076HCID 67098076, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl [(2R)-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-pyridyl)ethyl][2-[4′-[[[(cyanomethyl)sulfonyl]amino]carbonyl]-3′-(cyclohexyloxy)-4-biphenylyl]ethyl]carbamate (52.9 mg) in dimethyl sulfoxide (1.0 ml) was added potassium carbonate (28.3 mg), 30% aq. hydrogen peroxide solution (100 μl) at 0° C. After stirring for 16 hours at room temperature, 1N hydrochloric acid was added to the reaction mixture. The products were extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, and evaporated. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=95/5) to give tert-butyl [2-[4′-[[[(2-amino-2-oxoethyl)sulfonyl]amino]-carbonyl]-3′-(cyclohexyloxy)-4-biphenylyl]ethyl][(2R)-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-pyridyl)ethyl]-carbamate (30.0 mg).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-046130c10cda4c8d88187c51faaaaf4c
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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