Trifluoroacetic acid → HCID 67057042, compound

HRID 517509Notes

Reaction equation

HRID 517509 reaction equation
C(OC([NH:8][CH2:9][C@H:10]([N:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:17][CH2:16]1)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:8][CH2:9][C@H:10]([N:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[CH2:17][CH2:16]1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67056990HCID 67056990, compound

Product 1

HCID 67057042HCID 67057042, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 1 g (2.3 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-[4-(toluene-4-sulphonyl)piperazin-1-yl]propanoate in 10 ml of dichloromethane and 2.6 ml (3.4 mmol) of trifluoroacetic acid is stirred at ambient temperature for 18 h. After addition of a saturated aqueous solution of sodium hydrogen carbonate up to a pH of 8, the reaction medium is extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated. 780 mg (100%) of methyl (S)-3-amino-2-[4-(toluene-4-sulphonyl)piperazin-1-yl]propanoate are obtained in the form of an oil.

Workup

  1. extractionthe reaction medium is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-25075cfc053b4957999dd63c780e908e
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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