2,2,3,3,3-Pentafluoropropanol → 2(R)-(2,2,3,3,3-pentafluoropropylamino)-3-tritylsulfanylpropionic acid

HRID 2098229Notes

Reaction equation

HRID 2098229 reaction equation
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3]O.CCN(C(C)C)C(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[C:34]([S:53][CH2:54][C@@H:55]([C:57]([OH:59])=[O:58])[NH2:56])([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][NH:56][C@@H:55]([CH2:54][S:53][C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:57]([OH:59])=[O:58]

Participants

6

Reactant 4

HCID 98722,2,3,3,3-PentafluoropropanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 76044S-Trityl-L-CysteineHCID 81531Diisopropylethylamine

Product 1

HCID 866100972(R)-(2,2,3,3,3-pentafluoropropylamino)-3-tritylsulfanylpropionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. methylene chloride solution (75 mL) of 2,2,3,3,3-pentafluoropropan-1-ol (1.5 g, 10.0 mmol) and DIPEA (6.1 mL, 35.0 mmol) was added triflic anhydride (1.78 mL, 10.5 mmol). After 2.5 h, S-tritylcysteine was added all at once and the reaction mixture was stirred at 0° C. for 80 min. The reaction mixture was stirred at RT for 18 h and then concentrated on the rotovap. Ethyl acetate was added and the reaction mixture was washed with 1N HCl. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (3 hexanes/1 ethyl acetate+1% acetic acid) to provide 2(R)-(2,2,3,3,3-pentafluoropropylamino)-3-tritylsulfanylpropionic acid (3.29 g).

Workup

  1. stirringThe reaction mixture was stirred at RT for 18 h
  2. concentrationconcentrated on the rotovap
  3. additionEthyl acetate was added
  4. washthe reaction mixture was washed with 1N HCl
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (3 hexanes/1 ethyl acetate+1% acetic acid)

Sources & evidence

ORD record
ord-c7a1b95d23bd42fa84e1f7d8d33e6266
Source dataset
uspto-grants-2013_05
Patent number
US08450373B2

Reaction notes

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