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Hydrochloric Acid → (2R)-N-hydroxy-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanamide

HRID 84300
Notes
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Reaction equation

HRID 84300 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[N:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][N:17]([CH2:20][CH2:21][C@@:22]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[C:23]([NH:25][O:26]C4CCCCO4)=[O:24])[C:16](=[O:38])[CH:15]=3)=[CH:10][CH:9]=2)[N:4]=1.ClCCl.O.Cl>O1CCOCC1>[OH:26][NH:25][C:23](=[O:24])[C@:22]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:21][CH2:20][N:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([N:5]3[N:4]=[C:3]([O:2][CH3:1])[CH:7]=[N:6]3)=[CH:9][CH:10]=2)=[CH:15][C:16]1=[O:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 86671958(2R)-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86671959(2R)-N-hydroxy-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To (2R)-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (120 mg, 0.22 mmol) was added dioxane (2 ml), dichloromethane (2 ml), and water (1 ml). The reaction flask was cooled externally with ice then treated with a 4.0M sol of HCl in dioxane (0.55 ml). The reaction mixture was stirred for 15 minutes then concentrated under reduced pressure. IPA (10 ml) was added and concentrated to azeotrope any remaining water to furnish a tan solid (80 mg, 80% TY). MS (LC/MS) m/z 462.3 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.74 (s, 3 H) 2.34-2.51 (m, 1 H) 2.55-2.81 (m, 1 H) 3.13 (s, 3 H) 3.96-4.06 (m, 1 H) 4.07 (s, 3 H) 4.26-4.45 (m, 1 H) 6.84-7.00 (m, 2 H) 7.49 (s, 1 H) 7.75-7.93 (m, 3 H) 8.09 (d, J=8.78 Hz, 2 H)

Workup

  1. temperatureThe reaction flask was cooled externally with ice
  2. concentrationthen concentrated under reduced pressure
  3. additionIPA (10 ml) was added
  4. concentrationconcentrated
  5. customto furnish a tan solid (80 mg, 80% TY)

Sources & evidence

ORD record
ord-23521dc5d54547e48f6f3b62112194b8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846933B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes