HCID 90411479, compound → HCID 90412607, compound

HRID 1754602Notes

Reaction equation

HRID 1754602 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:21][N:22]1[CH:27]=[CH:26][C:25](=[O:28])[N:24](C(=O)C2C=CC=CC=2)[C:23]1=[O:37])[C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(C)[Na]>CO>[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:21][N:22]1[CH:27]=[CH:26][C:25](=[O:28])[NH:24][C:23]1=[O:37])[C@H:11]([O:13][Si:14]([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:15])[CH3:16])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 90411479HCID 90411479, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 90412607HCID 90412607, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 16 (about 4.6 mmol) in 100 ml of MeOH as added 2 ml of 25% NaOCH3 in MeOH. After being kept at room temperature for 15 hrs the reaction was quenched by adding 1.5 g of solid triethylammonium chloride and concentrated. The resulting material was partitioned between water and ethyl acetate. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated to an oil, which was then chromatographed on silica eluting with a gradient of ethyl acetate (33-50%) in hexane. Concentration of the pure product fractions afforded 1.7 g (about 88%) of 17 as a white crystalline solid. 1H NMR (DMSO-d6): δ 11.18 (s, 1H), 7.52 (d, J=7.8 Hz, 1H), 7.28 (m, 5H), 5.47 (d, J=7.8 Hz, 1H), 4.38 (s, 2H), 3.97 (m, 1H), 3.84 (m, 1H), 3.62 (m, 1H), 3.38 (m, 2H), 2.02 (m, 1H), 1.13 (d, J=5.7 Hz, 3H), 0.84 (s, 9H), 0.01 (s, 3H), 0.00 (s, 3H).

Workup

  1. customthe reaction was quenched
  2. additionby adding 1.5 g of solid triethylammonium chloride
  3. concentrationconcentrated
  4. customThe resulting material was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to an oil, which
  8. customwas then chromatographed on silica eluting with a gradient of ethyl acetate (33-50%) in hexane

Sources & evidence

ORD record
ord-128d409285f04a5cb7fa3f451bae4fae
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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