HCID 86607898, compound → HCID 57848917, compound

HRID 736800Notes

Reaction equation

HRID 736800 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C@@H:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C@@:6]([CH3:41])([C:33]([NH:35][O:36]C(C)(C)C)=[O:34])[CH2:5]1)(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([N:4]1[CH2:9][CH2:8][C@@H:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C@@:6]([CH3:41])([C:33]([NH:35][OH:36])=[O:34])[CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86607898HCID 86607898, compound

Product 1

HCID 57848917HCID 57848917, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

(3S,4R)-1-Acetyl-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (326 mg, 0.559 mmol) was dissolved in trifluoroacetic acid (5 mL) and heated at 40° C. overnight. The solvent was concentrated and the residual oil was treated with saturated aqueous NaHCO3 and extracted with ethyl acetate (3×). The combined organic extracts were dried over Na2SO4, then purified via column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give (3S,4R)-1-acetyl-N-hydroxy-3-methyl-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-3-carboxamide (70 mg, 0.133 mmol, 24%) as a colorless solid. LCMS (M−H): 1.58 min, 525.4; 1H NMR (400 MHz, MeOD) δ ppm 0.97 (s, 2H) 1.09-1.20 (m, 4H) 1.44 (d, J=13.14 Hz, 1H) 1.65-1.75 (m, 1H) 1.90-1.97 (m, 5H) 2.55 (d, J=14.40 Hz, 2H) 2.60-2.64 (m, 4H) 2.93-3.03 (m, 1H) 3.05-3.16 (m, 2H) 3.67 (s, 1H) 5.58 (s, 3H) 7.16 (d, J=9.09 Hz, 3H) 7.46-7.54 (m, 3H) 7.62-7.69 (m, 2H) 7.78 (dd, J=8.97, 2.15 Hz, 3H) 7.90 (d, J=8.59 Hz, 2H) 7.99 (d, J=8.08 Hz, 2H).

Workup

  1. concentrationThe solvent was concentrated
  2. additionthe residual oil was treated with saturated aqueous NaHCO3
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. custompurified via column chromatography on silica gel eluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-80af0ac2eb5a460fa2d2d875285a639c
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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