Sodium Bicarbonate → HCID 123708140, compound

HRID 1854569Notes

Reaction equation

HRID 1854569 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:20]([OH:22])[CH3:21])[C@H:12]([CH3:23])[N:11]1[C:24](=[O:34])[CH2:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:20]([C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[CH2:19][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[N:11]([C:24](=[O:34])[CH2:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33])[C@H:12]2[CH3:23])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 123453204HCID 123453204, compound

Product 1

HCID 123708140HCID 123708140, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (92 mg, 176 μmol, mixture of two diastereomers) in CH2Cl2 (1.8 mL). Add NaHCO3 (92 mg, 1.1 mmol) and 3,3,3-Triacetoxy-3-iodophthalide (90 mg, 211 μmol) at room temperature. Stir 40 min. Add saturated NaHCO3 solution and saturated Na2S2O3 solution, extract with ethyl acetate three times. Combine the ethyl acetate extracts, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 5-60%) to give the title compound as a white foam (0.068 g, 130 μmol). MS (m/z): 522 (M+1).

Workup

  1. customat room temperature
  2. extractionAdd saturated NaHCO3 solution and saturated Na2S2O3 solution, extract with ethyl acetate three times
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. customPurify the residue by silica gel chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-cacf9b76a46c4bfdaa89a1c6ca634786
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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