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

HRID 642905Notes

Reaction equation

HRID 642905 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-b42162db83e04225b7598bd37a55587f
Source dataset
uspto-grants-2010_04
Patent number
US07696250B2

Reaction notes

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