Ethyl Acetate → HCID 12082683, compound

HRID 1267570Notes

Reaction equation

HRID 1267570 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:37]SC)[C:6]([NH:8][C@@H:9]([CH3:36])[C:10]([NH:12][C@@H:13]([CH:33]([CH3:35])[CH3:34])[C:14]([NH:16][C@H:17]([C:22](=[O:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[O:11])=[O:7])(=[O:3])[CH3:2].O[O:41][S:42]([O-:44])=O.[K+].[CH3:46]COC(C)=O>CO.O>[C:1]([NH:4][C@@H:5]([CH2:37][S:42]([CH3:46])(=[O:44])=[O:41])[C:6]([NH:8][C@@H:9]([CH3:36])[C:10]([NH:12][C@@H:13]([CH:33]([CH3:35])[CH3:34])[C:14]([NH:16][C@H:17]([C:22](=[O:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[O:11])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 12082682HCID 12082682, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 12082683HCID 12082683, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The title compound from Example 201 (20 mg, 0.035 mmol) in 1 mL MeOH at OoC was treated with OXONE® (22 mg, 0.035 mmol) in 1 mL water. The mixture was allowed to warm to room temperature over 0.5 h and then poured into 30 mL EtOAc. Water was added, the layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over MgSO4, filtered and evaporated to give 6 mg of the title compound as colorless solid: 1H NMR (400 MHz, CD3OD) 8.14 (d, 1H, J=7.81 Hz), 7.75 (d, 1H, J=7.24 Hz), 7.25-7.05 (m, 5H), 4.94 (t, 1H, J=6.59 Hz), 4.62 (t, 1H, J=6.20 Hz), 4.35-4.20 (m, 1H), 4.15-4.05 (m, 1H), 3.78-3.70 (m, 1H), 3.48-3.38 (m, 1H), 3.29 (s, 3H), 2.88-2.80 (m, 1H), 2.75-2.45 (m, 5H), 2.15-2.03 (m, 1H), 1.97 (s, 3H), 1.90-1.80(m, 2H), 1.37 (d, 3H, J=7.26 Hz), 0.93 (d, 3H, J=6.77 Hz), 0.92 (d, 3H, J=6.74 Hz); MS (−APCI) m/z 595 (M−H)−.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4628e5b461c74c9f9a6804fcb8a9436a
Source dataset
uspto-grants-2003_04
Patent number
US06552168B1

Reaction notes

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