Methanol → HCID 11581279, compound

HRID 1725977Notes

Reaction equation

HRID 1725977 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[C:15]=1[C:24]([O:26][CH3:27])=[O:25])(=[O:12])=[O:11])([O-])=O.CO>[Ni].C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[C:15]=1[C:24]([O:26][CH3:27])=[O:25])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 887MethanolHCID 68863340HCID 68863340, compound

Product 1

HCID 11581279HCID 11581279, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 418B (2.0873 g, 5.35 mmol) in 4:1 methanol:ethyl acetate (120 mL) was treated with Raney nickel (4.00 g), pressurized to 60 psi with H2 and shaken for 2 hours. The reaction was then filtered and the filtrate was concentrated to yield the desired product (1.8750 g, 97%). MS (ESI(+)) m/e 361 (M+H)+, 383 (M+Na)+; MS (ESI(−)) m/e 359 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.32 (dd, 1H), 7.23 (td, 1H), 7.02 (d, 1H), 6.80 (m, 2H), 6.52 (td, 1H), 3.74 (s, 3H), 2.65 (m, 2H), 2.53 (m, 2H), 1.65 (m, 4H).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5bb9b752d3554213952a53b9f0b2fcec
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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