Acetic Acid → HCID 86607900, compound

HRID 736801Notes

Reaction equation

HRID 736801 reaction equation
[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2].CO.[C:41](O)(=O)[CH3:42].[C:45]([BH3-])#N.[Na+]>CC(C)=O>[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]([CH:41]([CH3:42])[CH3:45])[CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 86607899HCID 86607899, compound

Product 1

HCID 86607900HCID 86607900, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 324 mg (0.599 mmol) of (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (Example 47, Step 8) was added methanol (5 mL), acetic acid (300 μL), acetone (135 μL), and sodium cyanoborohydride (61 mg, 0.971 mmol) and the resulting reaction was stirred at room temperature overnight. The reaction mixture was then concentrated and the residue was taken up in saturated aqueous sodium carbonate and extracted with ethyl acetate (3×). the combined organic extracts were dried over Na2SO4 and purified using column chromatography on silica gel eluting with 1% methanol/CH2Cl2 to give (3S,4R)-N-tert-butoxy-1-isopropyl-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (205 mg, 0.352 mmol, 59%) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.91 (s, 3H) 1.05 (dd, J=6.57, 1.26 Hz, 5H) 1.23-1.26 (m, 8H) 1.55-1.64 (m, 4H) 1.95 (dd, J=13.64, 4.04 Hz, 1H) 2.09 (d, J=12.38 Hz, 1H) 2.27 (td, J=12.13, 3.03 Hz, 1H) 2.73-2.81 (m, 4H) 2.85 (d, J=4.29 Hz, 1H) 2.91-3.01 (m, 2H) 5.57 (d, J=1.01 Hz, 2H) 6.01 (d, J=7.33 Hz, 1H) 7.09 (ddd, J=9.41, 2.78, 2.46 Hz, 2H) 7.42 (s, 1H) 7.56 (ddd, J=8.34, 7.07, 1.26 Hz, 1H) 7.74 (ddd, J=8.46, 6.95, 1.26 Hz, 1H) 7.83-7.87 (m, 2H) 7.89-7.94 (m, 1H) 8.09 (d, J=7.83 Hz, 1H).

Workup

  1. customthe resulting reaction
  2. concentrationThe reaction mixture was then concentrated
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. custompurified

Sources & evidence

ORD record
ord-7b1745d869854df2a4533f5c144eab42
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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