Trifluoroacetic acid → HCID 57157131, compound

HRID 326386Notes

Reaction equation

HRID 326386 reaction equation
C(OC([NH:8][C@@H:9]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C@@H:10]([OH:19])[CH2:11][N:12]([CH3:18])[S:13](=[O:17])(=[O:16])[NH:14][CH3:15])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@@H:9]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C@@H:10]([OH:19])[CH2:11][N:12]([CH3:18])[S:13](=[O:17])(=[O:16])[NH:14][CH3:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22849141HCID 22849141, compound

Product 1

HCID 57157131HCID 57157131, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A sample of the resultant compound from Example 121 (501 mg, 1.27 mmol) was dissolved in 3 ml CH2Cl2, cooled to 0° C. under a dry nitrogen atmosphere, and treated with 3 ml trifluoroacetic acid. The solution was stirred for 5.5 h, then the solvents were removed under reduced pressure, and the residue was basified with 1.0M aq. Na2CO3. The product was extracted with 4×20 ml CH2Cl2. The combined extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to yield 332 mg (89%) of (2S,3S)-3-amino-4-cyclohexyl-2-hydroxy-1-(methyl(methylsulfamoyl)amino)butane as a white powder. 1H NMR (CDCl3) δ0.8-1.45 (several bm, 8H), 1.6-1.8 (bm, 5H), 1.9 (vbm, 3H), 2.75 (s, 3H), 2.85 (m, 1H), 2.94 (s, 3H), 3.21 (dd, 1H), 3.30 (dd, 1H), 3.48 (m, 1H). Mass spectrum: (M+H)+ =294.

Workup

  1. customthe solvents were removed under reduced pressure
  2. extractionThe product was extracted with 4×20 ml CH2Cl2
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-784a78a396774754bb200b7b1a174eeb
Source dataset
uspto-grants-1993_12
Patent number
US05268374

Reaction notes

Loading…