Ethyl Acetate → HCID 140240680, compound

HRID 705391Notes

Reaction equation

HRID 705391 reaction equation
[CH:1]1([C:4]2[C:5]([N:25]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:26][CH2:27][CH2:28]/[C:29](=[N:31]/[OH:32])/[NH2:30])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:20][CH:21]=[CH:22][N:23]=4)[C:8]=3[CH:24]=2)[CH2:3][CH2:2]1.[C:37](N1C=CN=C1)([N:39]1[CH:43]=[CH:42][N:41]=[CH:40]1)=[S:38].C(OCC)(=O)C>O1CCCC1>[N:39]1([C:37]([O:32]/[N:31]=[C:29](\[NH2:30])/[CH2:28][CH2:27][CH2:26][N:25]([C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:24][C:8]3[C:9]([C:19]4[NH:20][CH:21]=[CH:22][N:23]=4)=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[O:11][C:7]=3[CH:6]=2)[S:33]([CH3:36])(=[O:35])=[O:34])=[S:38])[CH:43]=[CH:42][N:41]=[CH:40]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 802641,1'-ThiocarbonyldiimidazoleHCID 89955243HCID 89955243, compound

Product 1

HCID 140240680HCID 140240680, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 176 (69.3 mg, 0.135 mmol) and 1,1′-thiocarbonyldiimidazole (38.1 mg, 0.203 mmol) in anhydrous tetrahydrofuran (1.3 mL) was stirred under nitrogen at 25° C. for 1.5 hours. Ethyl acetate (25 mL) was added, the mixture was washed with H2O (2×10 mL) and brine (10 mL), dried over anhydrous MgSO4, filtered, and concentrated by rotary evaporation to provide the title compound as a yellow foam (84 mg, 0.135 mmol, 100%).

Workup

  1. washthe mixture was washed with H2O (2×10 mL) and brine (10 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-79d7a7bdb4f8408a9b54d61998c2a1a9
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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