Water → HCID 53718173, compound

HRID 1268646Notes

Reaction equation

HRID 1268646 reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:20](=[O:37])[N:21]([CH3:36])[C@@H:22]([CH2:29][N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])[CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].O>ClCCl>[CH3:6][NH:7][C@H:8]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[C:20]([N:21]([CH3:36])[C@@H:22]([CH2:29][N:30]([CH3:35])[S:31]([CH3:34])(=[O:32])=[O:33])[CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=[O:37]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 54361148HCID 54361148, compound

Product 1

HCID 53718173HCID 53718173, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of of N-Methyl-N-((1R)-1-(N-methyl-N-((1R)-1-((N-methyl-N-(methylsufonyl)amino)methyl)-2-(2-thienyl)ethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamic acid tert-butyl ester (1.94 g, 3.37 mmol) in dichloromethane (7 ml) was cooled to 0° C. Trifluoroacetic acid (7 ml) was added. The reaction mixture was stirred for 45 min at 0° C. A saturated aqueous solution of sodium hydrogen carbonate (30 ml) was added. Solid sodium hydrogen carbonate was added until pH 7. Water (100 ml) was added, until a clear solution was obtained. The phases were separated. The aqueous solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (200 g), using dichloromethane/methanol/25% aqueous ammonia as eluent, to give 1.70 g of (2R)-2-Methylamino-N-methyl-N-((1R)-1-((N-methyl-N-(methylsulfonyl)amino)methyl)-2-(2-thienyl)ethyl)-3-(2-naphthyl)propionamide.

Workup

  1. customwas obtained
  2. customThe phases were separated
  3. extractionThe aqueous solution was extracted with dichloromethane (2×50 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (200 g)

Sources & evidence

ORD record
ord-dffdcc7d119e4947973908117995c4a6
Source dataset
uspto-grants-2003_04
Patent number
US06555570B2

Reaction notes

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