Water → HCID 67516730, compound

HRID 2201137Notes

Reaction equation

HRID 2201137 reaction equation
[NH2:1][C:2](=[O:20])[C@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH3:21][S:22]([O-:24])=[O:23].[Na+].CNCCNC.O>CS(C)=O.CCOC(C)=O>[NH2:1][C:2](=[O:20])[C@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 67516556HCID 67516556, compound

Product 1

HCID 67516730HCID 67516730, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate (200 mg, 0.512 mmol), sodium methanesulfinate (200 mg, 85%, 1.66 mmol), CuOTf hemi-toluene complex (120 mg, 0.464 mmol) and N,N′-dimethylethylenediamine (0.030 mL, 0.279 mmol) in DMSO (5 mL) was stirred at 115 C for 3 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-amino-3-(4-(methylsulfonyl)phenyl)-1-oxopropan-2-ylcarbamate (154 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d72d914716346d09b9f80d78bf8055b
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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