Thiourea → HCID 54757208, compound

HRID 632521Notes

Reaction equation

HRID 632521 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH2:24][CH:25]3[CH2:27]O3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:10][C:9]=1[O:28][CH2:29][O:30][CH3:31])([CH3:4])([CH3:3])[CH3:2].NC(N)=[S:35]>C(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH2:24][CH:25]3[CH2:27][S:35]3)(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:10][C:9]=1[O:28][CH2:29][O:30][CH3:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 54757207HCID 54757207, compound

Product 1

HCID 54757208HCID 54757208, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 20 (0.40 g, 0.86 mmol) in CH2Cl2 (5 mL) was added a mixture of thiourea (0.10 g, 1.3 mmol, 99%) in methanol (5 mL). The resulting mixture was stirred for 24 h at room temperature, after which the solvent was removed under reduced pressure. The residue was partitioned between CH2Cl2 and water. The organic layer was dried over anhydrous Na2SO4 and was filtered. Evaporation of solvent and purification by silica gel chromatography (hexanes/EtOAc=4/1) gave 0.34 g of 21 (83%). 1H NMR (500 MHz, CDCl3) δ 1.53 (s, 9H), 2.14 (dd, J=1.8, 5.0 Hz, 1H), 2.52 (dd, J=1.5, 5.9 Hz, 1H), 3.04 (dq, J=5.6, 7.8 Hz, 1H), 3.15 (dd, J=8.0, 14.2 Hz, 1H), 3.47 (s, 3H), 3.51 (dd, J=5.6, 14.4 Hz, 1H), 5.19 (s, 2H), 6.72 (dd, J=2.6, 8.8 Hz, 1H), 6.91 (d, J=2.6 Hz, 1H), 7.08-7.01 (m, 3H), 7.85-7.80 (m, 2H), 8.16-8.08 (m, 1H). 13C NMR (126 MHz, CDCl3) δ 24.4, 26.2, 28.5, 56.6, 62.7, 80.8, 95.3, 107.3, 114.1, 117.3, 119.4, 126.2, 130.8, 131.6, 146.6, 149.3, 152.8, 163.5. HRMS (FAB) calcd for C22H28NO7S2 (M+H+) 482.1302. found 482.1301.

Workup

  1. customafter which the solvent was removed under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and water
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationwas filtered
  5. customEvaporation of solvent and purification by silica gel chromatography (hexanes/EtOAc=4/1)

Sources & evidence

ORD record
ord-47cfce18bc6944439fc2036fd52b2fe4
Source dataset
uspto-grants-2016_04
Patent number
US09321754B2

Reaction notes

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