Trifluoroacetic acid → HCID 67061822, compound

HRID 910812Notes

Reaction equation

HRID 910812 reaction equation
C(OC([NH:8][NH:9][C:10](=[O:59])[CH2:11][C@H:12]1[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][O:25][CH2:26][C@@H:27]([CH3:31])[CH2:28][O:29][CH3:30])=[CH:20][CH:19]=2)[C@@H:15]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]3[O:42][CH2:41][CH2:40][N:39]([CH2:43][CH2:44][CH2:45][O:46][CH3:47])[C:38]=3[CH:48]=2)[CH2:14][N:13]1[S:49]([C:52]1[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=1)(=[O:51])=[O:50])=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:30][O:29][CH2:28][C@H:27]([CH3:31])[CH2:26][O:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C@@H:16]2[C@@H:15]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][C:37]4[O:42][CH2:41][CH2:40][N:39]([CH2:43][CH2:44][CH2:45][O:46][CH3:47])[C:38]=4[CH:48]=3)[CH2:14][N:13]([S:49]([C:52]3[CH:53]=[CH:54][C:55]([CH3:58])=[CH:56][CH:57]=3)(=[O:50])=[O:51])[C@@H:12]([CH2:11][C:10]([NH:9][NH2:8])=[O:59])[CH2:17]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67061890HCID 67061890, compound

Product 1

HCID 67061822HCID 67061822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1 mmol of N′-{2-[(2R,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetyl}-hydrazinecarboxylic acid tert-butyl ester in 13 ml of CH2Cl2 is treated at 0° C. with 3.3 ml of trifluoroacetic acid. The reaction mixture is stirred at 0° C. for 1 h, then at RT for 3 h and diluted with CH2Cl2, basified with saturated aqueous NaHCO3. The aqueous layer is extracted with CH2Cl2 (2×), the combined organic extracts are washed with H2O, then with brine, dried over Na2SO4, and concentrated under reduced pressure, affording the title compound as an orange oil. Rf=0.45 (CH2Cl2/MeOH/25% conc. NH3 200:20:1); Rt=4.57 (gradient I).

Workup

  1. waitat RT for 3 h
  2. extractionThe aqueous layer is extracted with CH2Cl2 (2×)
  3. washthe combined organic extracts are washed with H2O
  4. dry with materialwith brine, dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-019b9f89ae2841f581fd05f1a80c0717
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

Loading…