Lithium Hydroxide → HCID 10644970, compound

HRID 1755953Notes

Reaction equation

HRID 1755953 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][C:18]3[N:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:21][C:22]=3[CH3:23])=[CH:14][C:13]=2[CH:30]=1)[C:5]([OH:7])=[O:6])[CH3:2].C(O[C@H](C(N1[C@@H](CC2C=CC=CC=2)COC1=O)=O)CC1C=CC2OC(CC3N=C(C4C=CC=CC=4)OC=3C)=CC=2C=1)C.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:3][C@H:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][C:18]3[N:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:21][C:22]=3[CH3:23])=[CH:14][C:13]=2[CH:30]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 10530982HCID 10530982, compoundHCID 10692663HCID 10692663, compound

Product 1

HCID 10644970HCID 10644970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-Ethoxy-3-{2-[(5-methyl-2-phenyl-4-oxazolyl) methyl]benzofuran-5-yl}propanoic acid. 5-{(S)-2-Ethoxy-3-[(S)-4-benzyl-2-oxo-3-oxazolidinyl]-3-oxopropyl}-2-[(5-methyl-2-phenyl-4-oxazolyl) methyl]benzofuran (0.15 g, 0.26 mmol) was dissolved in tetrahydrofuran (5 ml). The solution was cooled to 0° C. and 0.5N lithium hydroxide (1.1 ml, 0.52 mmol) was added. After 15 minutes the bulk of the ethanol was removed, the residue was acidified with 1N HCl, diluted with water and extracted with ethyl acetate (3X). The combined extracts were washed with brine, dried over sodium sulfate and concentrated. The product was purified by flash chromatography (hexanes/ethyl acetate/acetic acid, 10:10:1) then recrystallized from hexanes/ethyl acetate and obtained as a white solid (48 mg, m.p. 129° C., [α]D =-12.5° (c 0.99, CDCl3)).

Workup

  1. customAfter 15 minutes the bulk of the ethanol was removed
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (3X)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (hexanes/ethyl acetate/acetic acid, 10:10:1)
  8. customthen recrystallized from hexanes/ethyl acetate
  9. customobtained as a white solid (48 mg, m.p. 129° C., [α]D =-12.5° (c 0.99, CDCl3))

Sources & evidence

ORD record
ord-b1bcef7cedaa4bf9b6c2171fdc088f3c
Source dataset
uspto-grants-1995_08
Patent number
US05438074

Reaction notes

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