Sodium Hydroxide → HCID 101025554, compound

HRID 1413119Notes

Reaction equation

HRID 1413119 reaction equation
[CH3:1][C@@H:2]([C@@H:32]([OH:34])[CH3:33])/[CH:3]=[CH:4]/[CH2:5][C@@H:6]1[C@@H:11]([OH:12])[C@@H:10]([OH:13])[C@H:9]([CH2:14]/[C:15](/[CH3:31])=[CH:16]/[C:17]([O:19]CCCCCCCCC(O)=O)=[O:18])[O:8][CH2:7]1.[OH-:35].[Na+]>>[CH3:1][C@@H:2]([C@@H:32]([OH:34])[CH3:33])[C:3]1[O:35][C:4]=1[CH2:5][C@@H:6]1[C@@H:11]([OH:12])[C@@H:10]([OH:13])[C@H:9]([CH2:14]/[C:15](/[CH3:31])=[CH:16]/[C:17]([OH:19])=[O:18])[O:8][CH2:7]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 10413058Pseudomonic acid C

Product 1

HCID 101025554HCID 101025554, compoundYield 74%

Procedure

Pseudomonic acid C (80 mgs) was dissolved in 0.1 M sodium hydroxide (20 ml) and stirred overnight at room temperature. After evaporation to low volume the solution was adjusted to pH 2 (5 M HCl), saturated with sodium chloride and extracted with ethyl acetate. The combined extracts were dried (MgSO4) then evaporated to dryness and chromatographed on silica (2 g) eluting with gradient of 0 to 8% methanol/chloroform. Fractions containing pure product (by hplc and tlc) were combined to give monic acid C (40 mgs, 74%), νmax (KBr) 3400 (broad) 1692 (broad), 1644, 1238, 975 cm-1 ; λmax (EtOH) 218 nm (ε9679); δH (CD3OD) 0.97 (3H, d, J 8 Hz, CH3 -17), 1.08 (3H, d, J 7 Hz, CH3 -14), 2.13 (3H, s, CH3 -15), 5.4 (2H, m, H-10, H-11), 5.67 (1H, s, H-2); δC (CD3OD) 170.2 (C1), 159.0 (C3), 135.8, 129.7 (C10, C11), 118.6 (C2), 76.2 (C5), 72.5 (C7), 71.6 (C13), 70.0 (C6), 65.8 (C16), 45.3 (C12), 44.1 (C4), 43.7 (C8), 33.7 (C9), 20.4 (C14), 19.3 (C15), 16.7 (C17). (Found: 284.1624. C16H28O6M.+ -C2H4O requires 284.1623).

Workup

  1. customAfter evaporation to low volume the solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthen evaporated to dryness
  5. customchromatographed on silica (2 g)
  6. washeluting with gradient of 0 to 8% methanol/chloroform
  7. additionFractions containing pure product (by hplc and tlc)

Sources & evidence

ORD record
ord-8240947a23594074b46010b33d6914a7
Source dataset
uspto-grants-1981_02
Patent number
US04248887

Reaction notes

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