Acetic Acid → HCID 54398842, compound

HRID 1857033Notes

Reaction equation

HRID 1857033 reaction equation
C[O-].[Na+].C(O)(=O)C.[CH2:8]([O:15][C:16]1[C:24]2[N:25]([CH3:29])[CH:26]=[C:27]([CH3:28])[C:23]=2[C:22]2[CH:21]([CH2:30][OH:31])[CH2:20][N:19](S(C)(=O)=O)[C:18]=2[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO.C1COCC1>[CH2:8]([O:15][C:16]1[C:24]2[N:25]([CH3:29])[CH:26]=[C:27]([CH3:28])[C:23]=2[C:22]2[C@H:21]([CH2:30][OH:31])[CH2:20][NH:19][C:18]=2[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium Methoxide2×HCID 54250254HCID 54250254, compound

Product 1

HCID 54398842HCID 54398842, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2b (3.3 g, 5.0 mmol) in a mixture of methanol (50 mL) and THF (30 mL) was added 5 mL of 1 M sodium methoxide in methanol. The reaction mixture was stirred for 5 hours, becoming a clear solution in approximately 30 min. Acetic acid (0.3 mL) was added to neutralize sodium methoxide, and the solution was evaporated to dryness. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Chromatography on silica gel, eluting with 5% acetone in CH2Cl2, afforded 1.6 g (85%) of (1S)-2a as a white solid. This product was shown by NMR and CHN analysis to be identical with the racemic material (2a). (1R)-2a was prepared analogously from 2c.

Workup

  1. customin approximately 30 min
  2. customthe solution was evaporated to dryness
  3. customThe residue was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. washChromatography on silica gel, eluting with 5% acetone in CH2Cl2
  8. customafforded 1.6 g (85%) of (1S)-2a as a white solid

Sources & evidence

ORD record
ord-825c7f25292143088033178228c860bb
Source dataset
uspto-grants-2000_11
Patent number
US06143877

Reaction notes

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