Acetic Acid → HCID 66890389, compound

HRID 254921Notes

Reaction equation

HRID 254921 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[S:24][C@@H:23]([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:33][CH2:34][CH2:35][O:36][CH3:37])[C@@H:21]1[OH:38])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C>C1COCC1>[CH3:37][O:36][CH2:35][CH2:34][O:33][C@@H:22]1[C@H:21]([OH:38])[C@@H:20]([CH2:19][OH:18])[S:24][C@H:23]1[N:25]1[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]1=[O:27]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 91173496HCID 91173496, compound

Product 1

HCID 66890389HCID 66890389, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound 114 (0.49 g, 0.88 mmol) in anhydrous THF (37 mL) 1M tetrabutylammonium fluoride in THF (1.8 mL) was added. Acetic acid (0.12 mL, 2.03 mmol) was added to this mixture and the resulting reaction mixture stirred at room temperature for 30 min. The solvent was removed under reduced pressure and the residue obtained was purified by flash silica gel column chromatography and eluted with acetone to yield Compound 51 (0.23 g, 83%). 1H NMR (300 MHz, DMSO-d6): 11.2 (s, 1H), 8.04 (d, 1H,), 5.94 (d, 1H), 5.69 (d, 1H), 5.20 (d, 1H), 4.15 (t, 1H), 4.04 (m, 1H), 3.67-3.53 (m, 6H), 3.47-3.36 (m, 2H), 3.31 (s, 3H); MS (API-ES) m/z 341.0 [M+Na]+.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. customthe residue obtained
  4. customwas purified by flash silica gel column chromatography
  5. washeluted with acetone

Sources & evidence

ORD record
ord-db6ae135722a4bda9af6cecdeeaaf15d
Source dataset
uspto-grants-2011_01
Patent number
US07875733B2

Reaction notes

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