HCID 57657323, compound → HCID 57657360, compound

HRID 1920763Notes

Reaction equation

HRID 1920763 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16](=[O:23])[NH:17][C:18]1[S:19][CH:20]=[CH:21][N:22]=1)[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:7][C@@H:8]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:16]([NH:17][C:18]1[S:19][CH:20]=[CH:21][N:22]=1)=[O:23]

Participants

3

Reactant 1

HCID 57657323HCID 57657323, compound

Product 1

HCID 57657360HCID 57657360, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound 12A (8.89 g, 25 mmol) in TFA (15 ml) was maintained at ambient temperature for 30 minutes. TFA was evaporated. Residue was dissolved in 5% aq. sodium bicarbonate (200 ml) and extracted with EtOAc (2×150 ml). Organic layer was washed with brine (150 ml), dried over anh. MgSO4 and evaporated in vacuum to provide target material (5.95 g, 94%) as light yellow solids. LC-MS [M+H] 254.1 (C12H19N3OS+H, requires 254.37).

Workup

  1. customTFA was evaporated
  2. dissolutionResidue was dissolved in 5% aq. sodium bicarbonate (200 ml)
  3. extractionextracted with EtOAc (2×150 ml)
  4. washOrganic layer was washed with brine (150 ml)
  5. dry with materialdried over anh. MgSO4
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-57c2b25b5db14d0489bc8dad14a5cf00
Source dataset
uspto-grants-2012_05
Patent number
US08173645B2

Reaction notes

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