Acetic Acid → HCID 54557580, compound

HRID 1290312Notes

Reaction equation

HRID 1290312 reaction equation
C([S:4][CH2:5][CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[C:16]([N+:28]([O-:30])=[O:29])[C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7])(=O)C.C1COCC1.C(O)(=O)C>CO.[Li+].[OH-]>[SH:4][CH2:5][CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[C:16]([N+:28]([O-:30])=[O:29])[C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 53802605HCID 53802605, compound

Product 1

HCID 54557580HCID 54557580, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

The thioacetate prepared in Example 9A (65 mg, 0.15 mmol) was dissolved in 2 mL methanol and 1 mL THF with 0.3 mL of IN LiOH. After stirring for 1 hour, 0.1 mL of acetic acid was added. The solution was extracted into ethyl acetate, washed with water and dried over magnesium sulfate. The product was dissolved into 1.0 ml acetic acid, heated to about 50° C. and concentrated in vacuo to give a light yellow solid (30 mg).

Workup

  1. extractionThe solution was extracted into ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. dissolutionThe product was dissolved into 1.0 ml acetic acid
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fbd6f1f425743529e5b30019fa2a9ca
Source dataset
uspto-grants-1998_05
Patent number
US05750744

Reaction notes

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