Trifluoroacetic acid → HCID 70048063, compound

HRID 1197929Notes

Reaction equation

HRID 1197929 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18]C(=O)OC(C)(C)C)[C@@H:9]([OH:17])[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[NH2:18][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@@H:9]([OH:17])[CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 86747488HCID 86747488, compound

Product 1

HCID 70048063HCID 70048063, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.41 g (1.16 mmol) of t-butyl [(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate was dissolved in 5 ml of methylene chloride, treated at 0° with 1.5 ml of 90% trifluoroacetic acid and subsequently stirred at room temperature for 5 hours. Thereafter, the reaction mixture was slowly added dropwise to 2N sodium carbonate solution, subsequently treated with 3N sodium hydroxide solution and finally extracted with methylene chloride. The methylene chloride extracts were dried over potassium carbonate and evaporated under reduced pressure, whereby there were obtained 249 mg of 1-[(2S,3S)-3-amino4-cyclohexyl-2-hydroxybutyl]-2-pyrrolidinone as an oil, MS: 255 (M+H)+.

Workup

  1. extractionfinally extracted with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over potassium carbonate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-146e9cf388f548f89ce69fa31b7941ea
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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