Trifluoroacetic acid → HCID 22951239, compound

HRID 276297Notes

Reaction equation

HRID 276297 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C@@H:13]([C@H:15]1[CH2:19][S:18][C:17](=[N:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=2[CH3:30])[N:16]1[CH2:31][CH:32]([CH3:34])[CH3:33])[CH3:14])(C)(C)C>>[OH:12][C@@H:13]([C@H:15]1[CH2:19][S:18][C:17](=[N:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=2[CH3:30])[N:16]1[CH2:31][CH:32]([CH3:34])[CH3:33])[CH3:14]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22951240HCID 22951240, compound

Product 1

HCID 22951239HCID 22951239, compoundYield 91.7%

Conditions

Temperature
20 °C

Procedure

A solution of TFA (8 mL) was cooled to 4° C. and added to solid (4S)-4-(1 (R)-tert-butoxyethyl)-3-isobutyl-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine (Method C5b; 0.16 g, 0.42 mmol) via cannula. The resulting solution was warmed to 20° C. and stirred at that temp. for 1.5 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between Et2O (100 mL) and a saturated NaHCO3 solution (100 mL). The ether layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography (SiO2; gradient from hexane to 10% EtOAc/hex) to yield (4S)-4-(1(R)-hydroxyethyl)-3-isobutyl-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine (0.13 g, 90%): TLC (25% EtOAc/hex) Rf0.13.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between Et2O (100 mL)
  3. dry with materialThe ether layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography (SiO2; gradient from hexane to 10% EtOAc/hex)

Sources & evidence

ORD record
ord-830014d13d134914a9a81bcfdb068b4c
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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