Acetic-formic anhydride → HCID 11245009, compound

HRID 887944Notes

Reaction equation

HRID 887944 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:14]([NH:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH3:15])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24](OC=O)(=[O:26])C>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:14]([N:16]([CH:24]=[O:26])[O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH3:15])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 57245995HCID 57245995, compound

Product 1

HCID 11245009HCID 11245009, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2R,3S)-2-(3-phenyl-1-propyl)-3-(2 tetrahydropyranyloxyamino)butanoic acid (21.4 g, 66.7 mmol) in pyridine (100 mL) at 0.degree. C. is added formic acetic anhydride (30 mL). The resulting solution is allowed to warm to 25.degree. C., stirred for 6 h, and then concentrated to dryness under reduced pressure. The resulting gum is dissolved in ethyl acetate (300 mL) and washed sequentially with 1 M hydrochloric acid (200 mL) and saturated aqueous sodium chloride solution. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2R,3S)-2-(3-Phenyl-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)butanoic acid as an oil (18.9 g, 81% yield).

Workup

  1. temperatureto warm to 25.degree
  2. concentrationconcentrated to dryness under reduced pressure
  3. dissolutionThe resulting gum is dissolved in ethyl acetate (300 mL)
  4. washwashed sequentially with 1 M hydrochloric acid (200 mL) and saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1a83255b2644ed18a3bd886781d1a8f
Source dataset
uspto-grants-2012_08
Patent number
US08247451B2

Reaction notes

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