HCID 117798829, compound → HCID 117798815, compound

HRID 1844324Notes

Reaction equation

HRID 1844324 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12](S(C3C=CC=CC=3)(=O)=O)[N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][O:26][Na]>C1COCC1>[CH3:25][O:26][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[N:11]=1

Participants

4

Reactant 2

HCID 117798829HCID 117798829, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 117798815HCID 117798815, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a N2 purged reactor is charged 5.0 g (13.9 mmol) of 4d and 50 mL of anhydrous THF. The resulting slurry is treated drop-wise with MeONa (25 wt % in MeOH) (1.1 equiv). The resulting slurry is stirred for 1 h at room temperature, and a complete conversion is observed by LC-MS. The slurry is filtered, washed with IPA; and dried in oven overnight at 50° C. to give 1.94 g 3d as a white solid. The mother liquor is concentrated, 15 mL of IPA is added, and the mixture warmed until complete dissolution. The mixture is cooled down to 10° C. and held for 1 h. A second crop of solid is collected by filtration, and dried to yield another 1.17 g of white solid 3d, total 90% yield; mp 74.6-75.8° C. 1H NMR (400 MHz, CDCl3) δ 8.12-8.09 (m, 2H), 7.78-7.73 (m, 2H), 7.64 (tt, J=7.4, 1.3 Hz, 1H), 7.58-7.53 (m, 2H), 6.88 (dd, J=7.7, 1.4 Hz, 1H), 3.87 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 164.0, 155.7, 139.7, 138.9, 133.6, 129.1, 128.9, 115.5, 114.9, 54.0; HRMS (ESI) m/z 250.0528 (M+H+), calc. for C12H12NO3S 250.0532.

Workup

  1. filtrationThe slurry is filtered
  2. washwashed with IPA
  3. customand dried in oven overnight at 50° C.

Sources & evidence

ORD record
ord-870b18d55c544b3a94c817dcd85b2ee9
Source dataset
uspto-grants-2015_02
Patent number
US08946418B1

Reaction notes

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