Water → HCID 10833541, compound

HRID 366140Notes

Reaction equation

HRID 366140 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@@H:16]([C:30](=[O:40])[N:31]([CH3:39])[CH2:32][CH2:33][C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)C)(C)(C)C.C(=O)([O-])O.[Na+].O>ClCCl>[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:19][C:18]([CH2:17][C@@H:16]([NH:14][CH3:13])[C:30]([N:31]([CH3:39])[CH2:32][CH2:33][C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)=[O:40])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 54249762HCID 54249762, compound

Product 1

HCID 10833541HCID 10833541, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., trifluoroacetic acid (4 ml) was added to a solution of N-((1R)-2-(biphenyl-4-yl)-1-(N-methyl-N-(2-(2-thienyl)ethyl)carbamoyl)ethyl)-N-methylcarbamic acid tert-butyl ester (910 mg, 1.90 mmol) in dichloromethane (4 ml). The reaction mixture was stirred for 3 h at 0° C. A saturated solution of sodium hydrogen carbonate (8 ml) was added. Solid sodium hydrogen carbonate was added, until pH 7 was obtained. Water was added, until a clear solution was obtained. The phases were separated. The aqueous phase was extracted with dichloromethane (2×30 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude produduct was purified by flash chromatogrphy on silica (60 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 674 mg of (2R)-3-(biphenyl-4-yl)-N-methyl-2-(methylamino)-N-(2-(2-thienyl)ethyl)propionamide.

Workup

  1. customwas obtained
  2. customwas obtained
  3. customThe phases were separated
  4. extractionThe aqueous phase was extracted with dichloromethane (2×30 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customThe crude produduct was purified by flash chromatogrphy on silica (60 g)

Sources & evidence

ORD record
ord-3e4d8ce643ce4ee68c41895a807367b1
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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