Water → HCID 19977493, compound

HRID 1451085Notes

Reaction equation

HRID 1451085 reaction equation
O.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:23]C)C=C4)N(CC2)C1.[CH2:60]([O:62][C:63](=[O:77])[C:64]1[CH:69]=[CH:68][C:67]([NH:70][C:71](=[O:73])[CH3:72])=[C:66](CC=C)[CH:65]=1)[CH3:61].S([O-])([O-])=O.[Na+].[Na+].[C:84]([OH:88])(C)([CH3:86])[CH3:85]>>[CH2:60]([O:62][C:63](=[O:77])[C:64]1[CH:69]=[CH:68][C:67]([NH:70][C:71](=[O:73])[CH3:72])=[C:66]([CH2:85][CH:84]([OH:88])[CH2:86][OH:23])[CH:65]=1)[CH3:61]

Participants

6

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 10586568HCID 10586568, compoundHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Product 1

HCID 19977493HCID 19977493, compoundYield 66%

Conditions

Temperature
0 °C

Procedure

To a solution of 1:1 water and tert-butanol (10 mL), AD-mix-α (Aldrich, 1.4 g) was added and the mixture stirred for 0.1 h. The mixture had two layers; the lower layer was yellow in color. To this mixture, ethyl-4-acetylamino-3-allylbenzoate (0.1 g, 0.0004 mol) was added in one portion and stirred at room temperature for 48 h. The reaction mixture was cooled to 0° C. and sodium sulphite (1.5 g, 0.0119 mol) was added. The reaction was stirred at 0° C. for 0.3 h and then at room temperature for 0.5 h. It was extracted with ethyl acetate (3×15 mL), the combined organic layers were dried over sodium sulphate, filtered, and concentrated. The residue was passed through a column of silica gel eluting first with 1:1 ethyl acetate:hexane to recover the starting material, and then with pure ethyl acetate to give 0.075 g (66%) of ethyl-4-acetylamino-3-(2',3'-dihydroxypropyl)benzoate (isomer A) as a white powder, mp 114°-116° C. The optical rotation of this solid was 0° at 589 nm.

Workup

  1. stirringstirred at room temperature for 48 h
  2. stirringThe reaction was stirred at 0° C. for 0.3 h
  3. waitat room temperature for 0.5 h
  4. extractionIt was extracted with ethyl acetate (3×15 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customhexane to recover the starting material

Sources & evidence

ORD record
ord-87dff55eb0c348c7a079130213731a2a
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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