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Water → (2R)-3-(Benzo[b]thiophen-3-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide

HRID 1268588
Notes
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Reaction equation

HRID 1268588 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:20](=[O:35])[N:21]([CH3:34])[C@@H:22]([C:30](=[O:33])[NH:31][CH3:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][C:11]1[C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[S:14][CH:15]=1)C)(C)(C)C.FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[S:14]1[CH:15]=[C:11]([CH2:10][C@@H:9]([NH:7][CH3:6])[C:20]([N:21]([CH3:34])[C@@H:22]([C:30](=[O:33])[NH:31][CH3:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:35])[C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 10839402((1R)-2-(Benzo[b]thiophen-3-yl)-1-(methyl-((1R)-1-methylcarbamoyl-2-phenyl-ethyl)carbamoyl)ethyl)-methylcarbamic acid tert-butylester

Product 1

HCID 10525588(2R)-3-(Benzo[b]thiophen-3-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide
Yield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

((1R)-2-(Benzo[b]thiophen-3-yl)-1-(methyl-((1R)-1-methylcarbamoyl-2-phenyl ethyl)carbamoyl)ethyl)-methylcarbamic acid tert-butylester (0.89 g; 1.70 mmol) was dissolved in methylene chloride (3 mL) and trifluoroacetic acid (2 mL) was added. is The reaction mixture was stirred for 45 min at room temperature. Water (5 mL) was added. Methylene chloride (5 mL), an aqueous solution of sodium hydrogen carbonate (saturated) and sodium hydrogen carbonate (solid) was added until pH 8. The aqueous phase was extracted with methylene chloride (3×10 mL). The combined organic phases were dried (magnesium sulfate) and evaporated in vacuo to afford 0.66 g of (2R)-3-(Benzo[b]thiophen-3-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide.

Workup

  1. extractionThe aqueous phase was extracted with methylene chloride (3×10 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-9e9ebba9ab49435e8e462c300362de89
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06555570B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes